feat: add device_id to flags request payload (#407)

* feat: add device_id to flags request payload

Add device_id parameter to all feature flag methods, similar to how
distinct_id is handled. The device_id is included in the flags request
payload sent to the server.

- Add device_id parameter to Client methods and module-level functions
- Add context support via set_context_device_id() for automatic fallback
- Add tests for explicit device_id and context-based device_id
- Bump version to 7.6.0

.env.example

@@ -0,0 +1,11 @@
+# PostHog API Configuration
+# Copy this file to .env and update with your actual values
+
+# Your project API key (found on the /setup page in PostHog)
+POSTHOG_PROJECT_API_KEY=phc_your_project_api_key_here
+
+# Your personal API key (for local evaluation and other advanced features)
+POSTHOG_PERSONAL_API_KEY=phx_your_personal_api_key_here
+
+# PostHog host URL (remove this line if using posthog.com)
+POSTHOG_HOST=http://localhost:8000

.github/dependabot.yml

@@ -0,0 +1,36 @@
+version: 2
+updates:
+  - package-ecosystem: "pip"
+    directory: "/"
+    schedule:
+      interval: "daily"
+      time: "10:00"
+      timezone: "UTC"
+    groups:
+      ai-providers:
+        patterns:
+          - "openai"
+          - "anthropic"
+          - "google-genai"
+          - "langchain-core"
+          - "langchain-community"
+          - "langchain-openai"
+          - "langchain-anthropic"
+          - "langgraph"
+    allow:
+      - dependency-name: "openai"
+      - dependency-name: "anthropic"
+      - dependency-name: "google-genai"
+      - dependency-name: "langchain-core"
+      - dependency-name: "langchain-community"
+      - dependency-name: "langchain-openai"
+      - dependency-name: "langchain-anthropic"
+      - dependency-name: "langgraph"
+    open-pull-requests-limit: 1
+    reviewers:
+      - "PostHog/team-llm-analytics"
+    # Uncomment below to enable auto-merge for minor updates when CI passes
+    # pull-request-branch-name:
+    #   separator: "/"
+    # assignees:
+    #   - "PostHog/ai-team"

.github/workflows/call-flags-project-board.yml

@@ -0,0 +1,17 @@
+# This workflow is used to call the flags-project-board workflow when a pull request is opened, ready for review, review requested, synchronized, converted to draft, or reopened.
+# It is used to update the feature flags project board with the pull request information.
+
+name: Call Feature Flags Project Workflow
+
+on:
+    pull_request:
+        types: [opened, ready_for_review, review_requested, synchronize, converted_to_draft, reopened]
+
+jobs:
+    call-flags-project:
+        uses: PostHog/.github/.github/workflows/flags-project-board.yml@main
+        with:
+            pr_number: ${{ github.event.pull_request.number }}
+            pr_node_id: ${{ github.event.pull_request.node_id }}
+            is_draft: ${{ github.event.pull_request.draft }}
+        secrets: inherit

.github/workflows/ci.yml

@@ -3,44 +3,42 @@ name: CI
 on:
     - pull_request
 
+permissions:
+    contents: read
+
 jobs:
     code-quality:
         name: Code quality checks
         runs-on: ubuntu-latest
 
         steps:
-            - uses: actions/checkout@v2
+            - uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
               with:
                   fetch-depth: 1
 
             - name: Set up Python 3.11
-              uses: actions/setup-python@v2
+              uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
               with:
                   python-version: 3.11.11
 
-            - uses: actions/cache@v3
+            - name: Install uv
+              uses: astral-sh/setup-uv@0c5e2b8115b80b4c7c5ddf6ffdd634974642d182 # v5.4.1
               with:
-                  path: ~/.cache/pip
-                  key: ${{ runner.os }}-pip-${{ hashFiles('setup.py') }}
-                  restore-keys: |
-                      ${{ runner.os }}-pip-
+                  enable-cache: true
+                  pyproject-file: 'pyproject.toml'
 
             - name: Install dev dependencies
+              shell: bash
               run: |
-                  python -m pip install -e .[dev]
-              if: steps.cache.outputs.cache-hit != 'true'
+                  UV_PROJECT_ENVIRONMENT=$pythonLocation uv sync --extra dev
 
-            - name: Check formatting with black
+            - name: Check formatting with ruff
               run: |
-                  black --check .
+                  ruff format --check .
 
-            - name: Lint with flake8
+            - name: Lint with ruff
               run: |
-                  flake8 posthog --ignore E501,W503
-
-            - name: Check import order with isort
-              run: |
-                  isort --check-only .
+                  ruff check .
 
             - name: Check types with mypy
               run: |
@@ -51,22 +49,83 @@ jobs:
         runs-on: ubuntu-latest
         strategy:
             matrix:
-                python-version: ['3.9', '3.10', '3.11', '3.12', '3.13']
+                python-version: ['3.10', '3.11', '3.12', '3.13', '3.14']
 
         steps:
-            - uses: actions/checkout@v2
+            - uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
               with:
                   fetch-depth: 1
 
             - name: Set up Python ${{ matrix.python-version }}
-              uses: actions/setup-python@v2
+              uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
               with:
                   python-version: ${{ matrix.python-version }}
 
-            - name: Install requirements.txt dependencies with pip
+            - name: Install uv
+              uses: astral-sh/setup-uv@0c5e2b8115b80b4c7c5ddf6ffdd634974642d182 # v5.4.1
+              with:
+                  enable-cache: true
+                  pyproject-file: 'pyproject.toml'
+
+            - name: Install test dependencies
+              shell: bash
               run: |
-                  python -m pip install -e .[test]
+                  UV_PROJECT_ENVIRONMENT=$pythonLocation uv sync --extra test
 
             - name: Run posthog tests
               run: |
                   pytest --verbose --timeout=30
+
+    import-check:
+        name: Python ${{ matrix.python-version }} import check
+        runs-on: ubuntu-latest
+        strategy:
+            matrix:
+                python-version: ['3.10', '3.11', '3.12', '3.13', '3.14']
+
+        steps:
+            - uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
+              with:
+                  fetch-depth: 1
+
+            - name: Set up Python ${{ matrix.python-version }}
+              uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
+              with:
+                  python-version: ${{ matrix.python-version }}
+
+            - name: Install posthog
+              run: pip install .
+
+            - name: Check import produces no warnings
+              run: python -W error -c "import posthog"
+
+    django5-integration:
+        name: Django 5 integration tests
+        runs-on: ubuntu-latest
+
+        steps:
+            - uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
+              with:
+                  fetch-depth: 1
+
+            - name: Set up Python 3.12
+              uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
+              with:
+                  python-version: 3.12
+
+            - name: Install uv
+              uses: astral-sh/setup-uv@0c5e2b8115b80b4c7c5ddf6ffdd634974642d182 # v5.4.1
+              with:
+                  enable-cache: true
+                  pyproject-file: 'integration_tests/django5/pyproject.toml'
+
+            - name: Install Django 5 test project dependencies
+              shell: bash
+              working-directory: integration_tests/django5
+              run: |
+                  UV_PROJECT_ENVIRONMENT=$pythonLocation uv sync
+
+            - name: Run Django 5 middleware integration tests
+              working-directory: integration_tests/django5
+              run: |
+                  uv run pytest test_middleware.py test_exception_capture.py --verbose

.github/workflows/codeql.yml

@@ -0,0 +1,45 @@
+name: 'CodeQL Advanced'
+
+on:
+  push:
+    branches: ['master']
+  pull_request:
+    branches: ['master']
+  schedule:
+    - cron: '32 13 * * 1'
+
+jobs:
+  analyze:
+    name: Analyze (${{ matrix.language }})
+    runs-on: 'ubuntu-latest'
+    permissions:
+      security-events: write
+      # required to fetch internal or private CodeQL packs
+      packages: read
+
+    strategy:
+      fail-fast: false
+      matrix:
+        include:
+          - language: actions
+            build-mode: none
+          - language: python
+            build-mode: none
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v6
+
+      - name: Initialize CodeQL
+        uses: github/codeql-action/init@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v4.31.9
+        with:
+          languages: ${{ matrix.language }}
+          build-mode: ${{ matrix.build-mode }}
+          # Disable TRAP caching - it creates a new cache per commit SHA which
+          # is never reused, causing wasted cache space.
+          # See: https://github.com/github/codeql-action/issues/2030
+          trap-caching: false
+
+      - name: Perform CodeQL Analysis
+        uses: github/codeql-action/analyze@5d4e8d1aca955e8d8589aabd499c5cae939e33c7 # v4.31.9
+        with:
+          category: '/language:${{matrix.language}}'

.github/workflows/generate-references.yml

@@ -0,0 +1,49 @@
+name: "Generate References"
+
+on:
+  workflow_dispatch:
+
+jobs:
+  docs-generation:
+    name: Generate references
+    runs-on: ubuntu-latest
+    permissions:
+      contents: write
+    steps:
+      - name: Checkout the repository
+        uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
+        with:
+          fetch-depth: 0
+
+      - name: Set up Python
+        uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
+        with:
+          python-version: 3.11.11
+
+      - name: Install uv
+        uses: astral-sh/setup-uv@0c5e2b8115b80b4c7c5ddf6ffdd634974642d182 # v5.4.1
+        with:
+            enable-cache: true
+            pyproject-file: 'pyproject.toml'
+
+      - name: Generate references
+        run: |
+          uv run bin/docs generate-references
+
+      - name: Check for changes in references
+        id: changes
+        run: |
+          if [ -n "$(git status --porcelain references/)" ]; then
+            echo "changed=true" >> $GITHUB_OUTPUT
+            echo "New references generated in references directory:"
+            git status --porcelain references/
+          else
+            echo "changed=false" >> $GITHUB_OUTPUT
+            echo "No new references generated in references directory"
+          fi
+
+      - uses: stefanzweifel/git-auto-commit-action@778341af668090896ca464160c2def5d1d1a3eb0
+        if: steps.changes.outputs.changed == 'true'
+        with:
+          commit_message: "Update generated references"
+          file_pattern: references/

.github/workflows/release.yaml

@@ -1,38 +0,0 @@
-name: 'Release'
-
-on:
-  - workflow_dispatch
-
-jobs:
-    release:
-        name: Publish release
-        runs-on: ubuntu-latest
-        env:
-            TWINE_USERNAME: __token__
-            TWINE_PASSWORD: ${{ secrets.PYPI_API_TOKEN }}
-        steps:
-            - name: Checkout the repository
-              uses: actions/checkout@v2
-              with:
-                  fetch-depth: 0
-                  token: ${{ secrets.POSTHOG_BOT_GITHUB_TOKEN }}
-
-            - name: Set up Python
-              uses: actions/setup-python@v2
-
-            - name: Detect version
-              run: echo "REPO_VERSION=$(python3 posthog/version.py)" >> $GITHUB_ENV
-
-            - name: Prepare for building release
-              run: pip install -U pip setuptools wheel twine
-
-            - name: Push release to PyPI
-              run: make release && make release_analytics
-
-            - name: Create GitHub release
-              uses: actions/create-release@v1
-              env:
-                  GITHUB_TOKEN: ${{ secrets.POSTHOG_BOT_GITHUB_TOKEN }}
-              with:
-                  tag_name: v${{ env.REPO_VERSION }}
-                  release_name: ${{ env.REPO_VERSION }}

.github/workflows/release.yml

@@ -0,0 +1,58 @@
+name: "Release"
+
+on:
+  push:
+    branches:
+      - master
+    paths:
+      - "posthog/version.py"
+  workflow_dispatch:
+
+jobs:
+  release:
+    name: Publish release
+    runs-on: ubuntu-latest
+    permissions:
+      contents: write
+      id-token: write
+    steps:
+      - name: Checkout the repository
+        uses: actions/checkout@85e6279cec87321a52edac9c87bce653a07cf6c2
+        with:
+          fetch-depth: 0
+
+      - name: Set up Python
+        uses: actions/setup-python@8d9ed9ac5c53483de85588cdf95a591a75ab9f55
+        with:
+          python-version: 3.11.11
+
+      - name: Install uv
+        uses: astral-sh/setup-uv@0c5e2b8115b80b4c7c5ddf6ffdd634974642d182 # v5.4.1
+        with:
+            enable-cache: true
+            pyproject-file: 'pyproject.toml'
+            
+      - name: Detect version
+        run: echo "REPO_VERSION=$(python3 posthog/version.py)" >> $GITHUB_ENV
+
+      - name: Prepare for building release
+        run: uv sync --extra dev
+
+      - name: Push releases to PyPI
+        env:
+          TWINE_USERNAME: __token__
+        run: uv run make release && uv run make release_analytics
+
+      - name: Create GitHub release
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          gh release create "v${{ env.REPO_VERSION }}" \
+            --title "${{ env.REPO_VERSION }}" \
+            --generate-notes
+      
+      - name: Dispatch generate-references for posthog-python
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          gh workflow run generate-references.yml --ref master

.gitignore

@@ -17,3 +17,6 @@ posthog-analytics
 .coverage
 pyrightconfig.json
 .env
+.DS_Store
+posthog-python-references.json
+.claude/settings.local.json

.pre-commit-config.yaml

@@ -1,9 +1,10 @@
 repos:
-  - repo: https://github.com/psf/black
-    rev: stable
-    hooks:
-    - id: black
-  - repo: https://github.com/pycqa/isort
-    rev: 5.7.0
-    hooks:
-      - id: isort
+- repo: https://github.com/astral-sh/ruff-pre-commit
+  # Ruff version.
+  rev: v0.11.12
+  hooks:
+    # Run the linter.
+    - id: ruff-check
+      args: [ --fix ]
+    # Run the formatter.
+    - id: ruff-format

BEFORE_SEND.md

@@ -0,0 +1,237 @@
+# Before Send Hook
+
+The `before_send` parameter allows you to modify or filter events before they are sent to PostHog. This is useful for:
+
+- **Privacy**: Removing or masking sensitive data (PII)
+- **Filtering**: Dropping unwanted events (test events, internal users, etc.)
+- **Enhancement**: Adding custom properties to all events
+- **Transformation**: Modifying event names or property formats
+
+## Basic Usage
+
+```python
+import posthog
+from typing import Optional, Dict, Any
+
+def my_before_send(event: Dict[str, Any]) -> Optional[Dict[str, Any]]:
+    """
+    Process event before sending to PostHog.
+    
+    Args:
+        event: The event dictionary containing 'event', 'distinct_id', 'properties', etc.
+    
+    Returns:
+        Modified event dictionary to send, or None to drop the event
+    """
+    # Your processing logic here
+    return event
+
+# Initialize client with before_send hook
+client = posthog.Client(
+    api_key="your-project-api-key",
+    before_send=my_before_send
+)
+```
+
+## Common Use Cases
+
+### 1. Filter Out Events
+
+```python
+from typing import Optional, Any
+
+def filter_events_by_property_or_event_name(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Drop events from internal users or test environments."""
+    properties = event.get("properties", {})
+    
+    # Choose some property from your events
+    event_source = properties.get("event_source", "")
+    if event_source.endswith("internal"):
+        return None  # Drop the event
+    
+    # Filter out test events
+    if event.get("event") == "test_event":
+        return None
+    
+    return event
+```
+
+### 2. Remove/Mask PII Data
+
+```python
+from typing import Optional, Any
+
+def scrub_pii(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Remove or mask personally identifiable information."""
+    properties = event.get("properties", {})
+    
+    # Mask email but keep domain for analytics
+    if "email" in properties:
+        email = properties["email"]
+        if "@" in email:
+            domain = email.split("@")[1]
+            properties["email"] = f"***@{domain}"
+        else:
+            properties["email"] = "***"
+    
+    # Remove sensitive fields entirely
+    sensitive_fields = ["my_business_info", "secret_things"]
+    for field in sensitive_fields:
+        properties.pop(field, None)
+    
+    return event
+```
+
+### 3. Add Custom Properties
+
+```python
+from typing import Optional, Any
+
+from datetime import datetime
+from typing import Optional, Any
+
+def add_context(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Add custom properties to all events."""
+    if "properties" not in event:
+        event["properties"] = {}
+    
+    event["properties"].update({
+        "app_version": "2.1.0",
+        "environment": "production", 
+        "processed_at": datetime.now().isoformat()
+    })
+    
+    return event
+```
+
+### 4. Transform Event Names
+
+```python
+from typing import Optional, Any
+
+def normalize_event_names(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Convert event names to a consistent format."""
+    original_event = event.get("event")
+    if original_event:
+        # Convert to snake_case
+        normalized = original_event.lower().replace(" ", "_").replace("-", "_")
+        event["event"] = f"app_{normalized}"
+    
+    return event
+```
+
+### 5. Log and drop in "dev" mode
+
+When running in local dev often, you want to log but drop all events
+
+
+```python
+from typing import Optional, Any
+
+def log_and_drop_all(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Convert event names to a consistent format."""
+    print(event)
+    
+    return None
+```
+
+### 6. Combined Processing
+
+```python
+from typing import Optional, Any
+
+def comprehensive_processor(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    """Apply multiple transformations in sequence."""
+    
+    # Step 1: Filter unwanted events
+    if should_drop_event(event):
+        return None
+    
+    # Step 2: Scrub PII
+    event = scrub_pii(event)
+    
+    # Step 3: Add context
+    event = add_context(event)
+    
+    # Step 4: Normalize names
+    event = normalize_event_names(event)
+    
+    return event
+
+def should_drop_event(event: dict[str, Any]) -> bool:
+    """Determine if event should be dropped."""
+    # Your filtering logic
+    return False
+```
+
+## Error Handling
+
+If your `before_send` function raises an exception, PostHog will:
+
+1. Log the error 
+2. Continue with the original, unmodified event
+3. Not crash your application
+
+```python
+from typing import Optional, Any
+
+def risky_before_send(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    # If this raises an exception, the original event will be sent
+    risky_operation()
+    return event
+```
+
+## Complete Example
+
+```python
+import posthog
+from typing import Optional, Any
+import re
+
+def production_before_send(event: dict[str, Any]) -> Optional[dict[str, Any]]:
+    try:
+        properties = event.get("properties", {})
+        
+        # 1. Filter out bot traffic
+        user_agent = properties.get("$user_agent", "")
+        if re.search(r'bot|crawler|spider', user_agent, re.I):
+            return None
+        
+        # 2. Filter out internal traffic  
+        ip = properties.get("$ip", "")
+        if ip.startswith("192.168.") or ip.startswith("10."):
+            return None
+        
+        # 3. Scrub email PII but keep domain
+        if "email" in properties:
+            email = properties["email"]
+            if "@" in email:
+                domain = email.split("@")[1]
+                properties["email"] = f"***@{domain}"
+        
+        # 4. Add custom context
+        properties.update({
+            "app_version": "1.0.0",
+            "build_number": "123"
+        })
+        
+        # 5. Normalize event name
+        if event.get("event"):
+            event["event"] = event["event"].lower().replace(" ", "_")
+        
+        return event
+        
+    except Exception as e:
+        # Log error but don't crash
+        print(f"Error in before_send: {e}")
+        return event  # Return original event on error
+
+# Usage
+client = posthog.Client(
+    api_key="your-api-key",
+    before_send=production_before_send
+)
+
+# All events will now be processed by your before_send function
+client.capture("user_123", "Page View", {"url": "/home"})
+```

CHANGELOG.md

@@ -1,3 +1,353 @@
+# 7.6.0 - 2026-01-12
+
+feat: add device_id to flags request payload
+
+Add device_id parameter to all feature flag methods, allowing the server to track device identifiers for flag evaluation. The device_id can be passed explicitly or set via context using `set_context_device_id()`.
+
+# 7.5.1 - 2026-01-07
+
+fix: avoid return from finally block to fix Python 3.14 SyntaxWarning (#361) - thanks @jodal
+
+# 7.5.0 - 2026-01-06
+
+feat: Capture Langchain, OpenAI and Anthropic errors as exceptions (if exception autocapture is enabled)
+feat: Add reference to exception in LLMA trace and span events
+
+# 7.4.3 - 2026-01-02
+
+Fixes cache creation cost for Langchain with Anthropic
+
+# 7.4.2 - 2025-12-22
+
+feat: add `in_app_modules` option to control code variables capturing
+
+# 7.4.1 - 2025-12-19
+
+fix: extract model from response for OpenAI stored prompts
+
+When using OpenAI stored prompts, the model is defined in the OpenAI dashboard rather than passed in the API request. This fix adds a fallback to extract the model from the response object when not provided in kwargs, ensuring generations show up with the correct model and enabling cost calculations.
+
+# 7.4.0 - 2025-12-16
+
+feat: Add automatic retries for feature flag requests
+
+Feature flag API requests now automatically retry on transient failures:
+
+- Network errors (connection refused, DNS failures, timeouts)
+- Server errors (500, 502, 503, 504)
+- Up to 2 retries with exponential backoff (0.5s, 1s delays)
+
+Rate limit (429) and quota (402) errors are not retried.
+
+# 7.3.1 - 2025-12-06
+
+fix: remove unused $exception_message and $exception_type
+
+# 7.3.0 - 2025-12-05
+
+feat: improve code variables capture masking
+
+# 7.2.0 - 2025-12-01
+
+feat: add $feature_flag_evaluated_at properties to $feature_flag_called events
+
+# 7.1.0 - 2025-11-26
+
+Add support for the async version of Gemini.
+
+# 7.0.2 - 2025-11-18
+
+Add support for Python 3.14.
+Projects upgrading to Python 3.14 should ensure any Pydantic models passed into the SDK use Pydantic v2, as Pydantic v1 is not compatible with Python 3.14.
+
+# 7.0.1 - 2025-11-15
+
+Try to use repr() when formatting code variables
+
+# 7.0.0 - 2025-11-11
+
+NB Python 3.9 is no longer supported
+
+- chore(llma): update LLM provider SDKs to latest major versions
+  - openai: 1.102.0 → 2.7.1
+  - anthropic: 0.64.0 → 0.72.0
+  - google-genai: 1.32.0 → 1.49.0
+  - langchain-core: 0.3.75 → 1.0.3
+  - langchain-openai: 0.3.32 → 1.0.2
+  - langchain-anthropic: 0.3.19 → 1.0.1
+  - langchain-community: 0.3.29 → 0.4.1
+  - langgraph: 0.6.6 → 1.0.2
+
+# 6.9.3 - 2025-11-10
+
+- feat(ph-ai): PostHog properties dict in GenerationMetadata
+
+# 6.9.2 - 2025-11-10
+
+- fix(llma): fix cache token double subtraction in Langchain for non-Anthropic providers causing negative costs
+
+# 6.9.1 - 2025-11-07
+
+- fix(error-tracking): pass code variables config from init to client
+
+# 6.9.0 - 2025-11-06
+
+- feat(error-tracking): add local variables capture
+
+# 6.8.0 - 2025-11-03
+
+- feat(llma): send web search calls to be used for LLM cost calculations
+
+# 6.7.14 - 2025-11-03
+
+- fix(django): Handle request.user access in async middleware context to prevent SynchronousOnlyOperation errors in Django 5+ (fixes #355)
+- test(django): Add Django 5 integration test suite with real ASGI application testing async middleware behavior
+
+# 6.7.13 - 2025-11-02
+
+- fix(llma): cache cost calculation in the LangChain callback
+
+# 6.7.12 - 2025-11-02
+
+- fix(django): Restore process_exception method to capture view and downstream middleware exceptions (fixes #329)
+- fix(ai/langchain): Add LangChain 1.0+ compatibility for CallbackHandler imports (fixes #362)
+
+# 6.7.11 - 2025-10-28
+
+- feat(ai): Add `$ai_framework` property for framework integrations (e.g. LangChain)
+
+# 6.7.10 - 2025-10-24
+
+- fix(django): Make middleware truly hybrid - compatible with both sync (WSGI) and async (ASGI) Django stacks without breaking sync-only deployments
+
+# 6.7.9 - 2025-10-22
+
+- fix(flags): multi-condition flags with static cohorts returning wrong variants
+
+# 6.7.8 - 2025-10-16
+
+- fix(llma): missing async for OpenAI's streaming implementation
+
+# 6.7.7 - 2025-10-14
+
+- fix: remove deprecated attribute $exception_personURL from exception events
+
+# 6.7.6 - 2025-09-16
+
+- fix: don't sort condition sets with variant overrides to the top
+- fix: Prevent core Client methods from raising exceptions
+
+# 6.7.5 - 2025-09-16
+
+- feat: Django middleware now supports async request handling.
+
+# 6.7.4 - 2025-09-05
+
+- fix: Missing system prompts for some providers
+
+# 6.7.3 - 2025-09-04
+
+- fix: missing usage tokens in Gemini
+
+# 6.7.2 - 2025-09-03
+
+- fix: tool call results in streaming providers
+
+# 6.7.1 - 2025-09-01
+
+- fix: Add base64 inline image sanitization
+
+# 6.7.0 - 2025-08-26
+
+- feat: Add support for feature flag dependencies
+
+# 6.6.1 - 2025-08-21
+
+- fix: Prevent `NoneType` error when `group_properties` is `None`
+
+# 6.6.0 - 2025-08-15
+
+- feat: Add `flag_keys_to_evaluate` parameter to optimize feature flag evaluation performance by only evaluating specified flags
+- feat: Add `flag_keys_filter` option to `send_feature_flags` for selective flag evaluation in capture events
+
+# 6.5.0 - 2025-08-08
+
+- feat: Add `$context_tags` to an event to know which properties were included as tags
+
+# 6.4.1 - 2025-08-06
+
+- fix: Always pass project API key in `remote_config` requests for deterministic project routing
+
+# 6.4.0 - 2025-08-05
+
+- feat: support Vertex AI for Gemini
+
+# 6.3.4 - 2025-08-04
+
+- fix: set `$ai_tools` for all providers and `$ai_output_choices` for all non-streaming provider flows properly
+
+# 6.3.3 - 2025-08-01
+
+- fix: `get_feature_flag_result` now correctly returns FeatureFlagResult when payload is empty string instead of None
+
+# 6.3.2 - 2025-07-31
+
+- fix: Anthropic's tool calls are now handled properly
+
+# 6.3.0 - 2025-07-22
+
+- feat: Enhanced `send_feature_flags` parameter to accept `SendFeatureFlagsOptions` object for declarative control over local/remote evaluation and custom properties
+
+# 6.2.1 - 2025-07-21
+
+- feat: make `posthog_client` an optional argument in PostHog AI providers wrappers (`posthog.ai.*`), intuitively using the default client as the default
+
+# 6.1.1 - 2025-07-16
+
+- fix: correctly capture exceptions processed by Django from views or middleware
+
+# 6.1.0 - 2025-07-10
+
+- feat: decouple feature flag local evaluation from personal API keys; support decrypting remote config payloads without relying on the feature flags poller
+
+# 6.0.4 - 2025-07-09
+
+- fix: add POSTHOG_MW_CLIENT setting to django middleware, to support custom clients for exception capture.
+
+# 6.0.3 - 2025-07-07
+
+- feat: add a feature flag evaluation cache (local storage or redis) to support returning flag evaluations when the service is down
+
+# 6.0.2 - 2025-07-02
+
+- fix: send_feature_flags changed to default to false in `Client::capture_exception`
+
+# 6.0.1
+
+- fix: response `$process_person_profile` property when passed to capture
+
+# 6.0.0
+
+This release contains a number of major breaking changes:
+
+- feat: make distinct_id an optional parameter in posthog.capture and related functions
+- feat: make capture and related functions return `Optional[str]`, which is the UUID of the sent event, if it was sent
+- fix: remove `identify` (prefer `posthog.set()`), and `page` and `screen` (prefer `posthog.capture()`)
+- fix: delete exception-capture specific integrations module. Prefer the general-purpose django middleware as a replacement for the django `Integration`.
+
+To migrate to this version, you'll mostly just need to switch to using named keyword arguments, rather than positional ones. For example:
+
+```python
+# Old calling convention
+posthog.capture("user123", "button_clicked", {"button_id": "123"})
+# New calling convention
+posthog.capture(distinct_id="user123", event="button_clicked", properties={"button_id": "123"})
+
+# Better pattern
+with posthog.new_context():
+    posthog.identify_context("user123")
+
+    # The event name is the first argument, and can be passed positionally, or as a keyword argument in a later position
+    posthog.capture("button_pressed")
+```
+
+Generally, arguments are now appropriately typed, and docstrings have been updated. If something is unclear, please open an issue, or submit a PR!
+
+# 5.4.0 - 2025-06-20
+
+- feat: add support to session_id context on page method
+
+# 5.3.0 - 2025-06-19
+
+- fix: safely handle exception values
+
+# 5.2.0 - 2025-06-19
+
+- feat: construct artificial stack traces if no traceback is available on a captured exception
+
+## 5.1.0 - 2025-06-18
+
+- feat: session and distinct ID's can now be associated with contexts, and are used as such
+- feat: django http request middleware
+
+## 5.0.0 - 2025-06-16
+
+- fix: removed deprecated sentry integration
+
+## 4.10.0 - 2025-06-13
+
+- fix: no longer fail in autocapture.
+
+## 4.9.0 - 2025-06-13
+
+- feat(ai): track reasoning and cache tokens in the LangChain callback
+
+## 4.8.0 - 2025-06-10
+
+- fix: export scoped, rather than tracked, decorator
+- feat: allow use of contexts without error tracking
+
+## 4.7.0 - 2025-06-10
+
+- feat: add support for parse endpoint in responses API (no longer beta)
+
+## 4.6.2 - 2025-06-09
+
+- fix: replace `import posthog` with direct method imports
+
+## 4.6.1 - 2025-06-09
+
+- fix: replace `import posthog` in `posthoganalytics` package
+
+## 4.6.0 - 2025-06-09
+
+- feat: add additional user and request context to captured exceptions via the Django integration
+- feat: Add `setup()` function to initialise default client
+
+## 4.5.0 - 2025-06-09
+
+- feat: add before_send callback (#249)
+
+## 4.4.2- 2025-06-09
+
+- empty point release to fix release automation
+
+## 4.4.1 2025-06-09
+
+- empty point release to fix release automation
+
+## 4.4.0 - 2025-06-09
+
+- Use the new `/flags` endpoint for all feature flag evaluations (don't fall back to `/decide` at all)
+
+## 4.3.2 - 2025-06-06
+
+1. Add context management:
+
+- New context manager with `posthog.new_context()`
+- Tag functions: `posthog.tag()`, `posthog.get_tags()`, `posthog.clear_tags()`
+- Function decorator:
+  - `@posthog.scoped` - Creates context and captures exceptions thrown within the function
+- Automatic deduplication of exceptions to ensure each exception is only captured once
+
+2. fix: feature flag request use geoip_disable (#235)
+3. chore: pin actions versions (#210)
+4. fix: opinionated setup and clean fn fix (#240)
+5. fix: release action failed (#241)
+
+## 4.2.0 - 2025-05-22
+
+Add support for google gemini
+
+## 4.1.0 - 2025-05-22
+
+Moved ai openai package to a composition approach over inheritance.
+
+## 4.0.1 – 2025-04-29
+
+1. Remove deprecated `monotonic` library. Use Python's core `time.monotonic` function instead
+2. Clarify Python 3.9+ is required
+
 ## 4.0.0 - 2025-04-24
 
 1. Added new method `get_feature_flag_result` which returns a `FeatureFlagResult` object. This object breaks down the result of a feature flag into its enabled state, variant, and payload. The benefit of this method is it allows you to retrieve the result of a feature flag and its payload in a single API call. You can call `get_value` on the result to get the value of the feature flag, which is the same value returned by `get_feature_flag` (aka the string `variant` if the flag is a multivariate flag or the `boolean` value if the flag is a boolean flag).

Makefile

@@ -1,6 +1,5 @@
 lint:
-	pylint --rcfile=.pylintrc --reports=y --exit-zero analytics | tee pylint.out
-	flake8 --max-complexity=10 --statistics analytics > flake8.out || true
+	uvx ruff format
 
 test:
 	coverage run -m pytest
@@ -17,22 +16,42 @@ release_analytics:
 	rm -rf posthoganalytics
 	mkdir posthoganalytics
 	cp -r posthog/* posthoganalytics/
-	find ./posthoganalytics -type f -exec sed -i '' -e 's/from posthog /from posthoganalytics /g' {} \;
-	find ./posthoganalytics -type f -exec sed -i '' -e 's/from posthog\./from posthoganalytics\./g' {} \;
+	find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthog /from posthoganalytics /g' {} \;
+	find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthog\./from posthoganalytics\./g' {} \;
+	find ./posthoganalytics -name "*.bak" -delete
 	rm -rf posthog
 	python setup_analytics.py sdist bdist_wheel
 	twine upload dist/*
 	mkdir posthog
-	find ./posthoganalytics -type f -exec sed -i '' -e 's/from posthoganalytics /from posthog /g' {} \;
-	find ./posthoganalytics -type f -exec sed -i '' -e 's/from posthoganalytics\./from posthog\./g' {} \;
+	find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthoganalytics /from posthog /g' {} \;
+	find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthoganalytics\./from posthog\./g' {} \;
+	find ./posthoganalytics -name "*.bak" -delete
 	cp -r posthoganalytics/* posthog/
 	rm -rf posthoganalytics
+	rm -f pyproject.toml
+	cp pyproject.toml.backup pyproject.toml
+	rm -f pyproject.toml.backup
 
 e2e_test:
 	.buildscripts/e2e.sh
 
-django_example:
-	python -m pip install -e ".[sentry]"
-	cd sentry_django_example && python manage.py runserver 8080
+prep_local:
+	rm -rf ../posthog-python-local
+	mkdir ../posthog-python-local
+	cp -r . ../posthog-python-local/
+	cd ../posthog-python-local && rm -rf dist build posthoganalytics .git
+	cd ../posthog-python-local && mkdir posthoganalytics
+	cd ../posthog-python-local && cp -r posthog/* posthoganalytics/
+	cd ../posthog-python-local && find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthog /from posthoganalytics /g' {} \;
+	cd ../posthog-python-local && find ./posthoganalytics -type f -name "*.py" -exec sed -i.bak -e 's/from posthog\./from posthoganalytics\./g' {} \;
+	cd ../posthog-python-local && find ./posthoganalytics -name "*.bak" -delete
+	cd ../posthog-python-local && rm -rf posthog
+	cd ../posthog-python-local && sed -i.bak 's/from version import VERSION/from posthoganalytics.version import VERSION/' setup_analytics.py
+	cd ../posthog-python-local && rm setup_analytics.py.bak
+	cd ../posthog-python-local && sed -i.bak 's/"posthog"/"posthoganalytics"/' setup.py
+	cd ../posthog-python-local && rm setup.py.bak
+	cd ../posthog-python-local && python -c "import setup_analytics" 2>/dev/null || true
+	@echo "Local copy created at ../posthog-python-local"
+	@echo "Install with: pip install -e ../posthog-python-local"
 
-.PHONY: test lint release e2e_test
+.PHONY: test lint release e2e_test prep_local

README.md

@@ -1,48 +1,74 @@
 # PostHog Python
 
-[![PyPI](https://img.shields.io/pypi/v/posthog)](https://pypi.org/project/posthog/)
-
+<p align="center">
+  <img alt="posthoglogo" src="https://user-images.githubusercontent.com/65415371/205059737-c8a4f836-4889-4654-902e-f302b187b6a0.png">
+</p>
+<p align="center">
+   <a href="https://pypi.org/project/posthog/"><img alt="pypi installs" src="https://img.shields.io/pypi/v/posthog"/></a>
+   <img alt="GitHub contributors" src="https://img.shields.io/github/contributors/posthog/posthog-python">
+  <img alt="GitHub commit activity" src="https://img.shields.io/github/commit-activity/m/posthog/posthog-python"/>
+  <img alt="GitHub closed issues" src="https://img.shields.io/github/issues-closed/posthog/posthog-python"/>
+</p>
 
 Please see the [Python integration docs](https://posthog.com/docs/integrations/python-integration) for details.
 
+## Python Version Support
+
+| SDK Version | Python Versions Supported | Notes |
+|-------------|---------------------------|-------|
+| 7.3.1+      | 3.10, 3.11, 3.12, 3.13, 3.14 | Added Python 3.14 support |
+| 7.0.0 - 7.0.1 | 3.10, 3.11, 3.12, 3.13  | Dropped Python 3.9 support |
+| 4.0.1 - 6.x | 3.9, 3.10, 3.11, 3.12, 3.13 | Python 3.9+ required |
+
 ## Development
 
 ### Testing Locally
 
-1. Run `python3 -m venv env` (creates virtual environment called "env")
-    * or `uv venv env`
+We recommend using [uv](https://docs.astral.sh/uv/). It's super fast.
+
+1. Run `uv venv env` (creates virtual environment called "env")
+    * or `python3 -m venv env`
 2. Run `source env/bin/activate` (activates the virtual environment)
-3. Run `python3 -m pip install -e ".[test]"` (installs the package in develop mode, along with test dependencies)
-    * or `uv pip install -e ".[test]"`
-4. Run `make test`
+3. Run `uv sync --extra dev --extra test` (installs the package in develop mode, along with test dependencies)
+    * or `pip install -e ".[dev,test]"`
+4. you have to run `pre-commit install` to have auto linting pre commit
+5. Run `make test`
   1. To run a specific test do `pytest -k test_no_api_key`
 
+## PostHog recommends `uv` so...
+
+```bash
+uv python install 3.12
+uv python pin 3.12
+uv venv
+source env/bin/activate
+uv sync --extra dev --extra test
+pre-commit install
+make test
+```
+
 ### Running Locally
 
 Assuming you have a [local version of PostHog](https://posthog.com/docs/developing-locally) running, you can run `python3 example.py` to see the library in action.
 
-### Running the Django Sentry Integration Locally
-
-There's a sample Django project included, called `sentry_django_example`, which explains how to use PostHog with Sentry.
-
-There's 2 places of importance (Changes required are all marked with TODO in the sample project directory)
-
-1. Settings.py
-    1. Input your Sentry DSN
-    2. Input your Sentry Org and ProjectID details into `PosthogIntegration()`
-    3. Add `POSTHOG_DJANGO` to settings.py. This allows the `PosthogDistinctIdMiddleware` to get the distinct_ids
-
-2. urls.py
-    1. This includes the `sentry-debug/` endpoint, which generates an exception
-
-To run things: `make django_example`. This installs the posthog-python library with the sentry-sdk add-on, and then runs the django app.
-Also start the PostHog app locally.
-Then navigate to `http://127.0.0.1:8080/sentry-debug/` and you should get an event in both Sentry and PostHog, with links to each other.
-
 ### Releasing Versions
 
-Updated are released using GitHub Actions: after bumping `version.py` in `master` and adding to `CHANGELOG.md`, go to [our release workflow's page](https://github.com/PostHog/posthog-python/actions/workflows/release.yaml) and dispatch it manually, using workflow from `master`.
+Updates are released automatically using GitHub Actions when `version.py` is updated on `master`. After bumping `version.py` in `master` and adding to `CHANGELOG.md`, the [release workflow](https://github.com/PostHog/posthog-python/blob/master/.github/workflows/release.yaml) will automatically trigger and deploy the new version.
 
-## Questions?
+If you need to check the latest runs or manually trigger a release, you can go to [our release workflow's page](https://github.com/PostHog/posthog-python/actions/workflows/release.yaml) and dispatch it manually, using workflow from `master`.
 
-### [Join our Slack community.](https://join.slack.com/t/posthogusers/shared_invite/enQtOTY0MzU5NjAwMDY3LTc2MWQ0OTZlNjhkODk3ZDI3NDVjMDE1YjgxY2I4ZjI4MzJhZmVmNjJkN2NmMGJmMzc2N2U3Yjc3ZjI5NGFlZDQ)
+
+### Testing changes locally with the PostHog app
+
+You can run `make prep_local`, and it'll create a new folder alongside the SDK repo one called `posthog-python-local`, which you can then import into the posthog project by changing pyproject.toml to look like this:
+```toml
+dependencies = [
+    ...
+    "posthoganalytics" #NOTE: no version number
+    ...
+]
+...
+[tools.uv.sources]
+posthoganalytics = { path = "../posthog-python-local" }
+```
+This'll let you build and test SDK changes fully locally, incorporating them into your local posthog app stack. It mainly takes care of the `posthog -> posthoganalytics` module renaming. You'll need to re-run `make prep_local` each time you make a change, and re-run `uv sync --active` in the posthog app project.

bin/docs

@@ -0,0 +1,8 @@
+#!/usr/bin/env bash
+#/ Usage: bin/docs
+#/ Description: Generate documentation for the PostHog Python SDK
+source bin/helpers/_utils.sh
+set_source_and_root_dir
+ensure_virtual_env
+
+exec python3 "$(dirname "$0")/docs_scripts/generate_json_schemas.py" "$@" 

bin/docs_scripts/doc_constant.py

@@ -0,0 +1,43 @@
+"""
+Constants for PostHog Python SDK documentation generation.
+"""
+
+from typing import Dict, Union
+from posthog.version import VERSION
+
+# Documentation generation metadata
+DOCUMENTATION_METADATA = {
+    "hogRef": "0.3",
+    "slugPrefix": "posthog-python",
+    "specUrl": "https://github.com/PostHog/posthog-python",
+}
+
+# Docstring parsing patterns for new format
+DOCSTRING_PATTERNS = {
+    "examples_section": r"Examples:\s*\n(.*?)(?=\n\s*\n\s*Category:|\Z)",
+    "args_section": r"Args:\s*\n(.*?)(?=\n\s*\n\s*Examples:|\n\s*\n\s*Details:|\n\s*\n\s*Category:|\Z)",
+    "details_section": r"Details:\s*\n(.*?)(?=\n\s*\n\s*Examples:|\n\s*\n\s*Category:|\Z)",
+    "category_section": r"Category:\s*\n\s*(.+?)\s*(?:\n|$)",
+    "code_block": r"```(?:python)?\n(.*?)```",
+    "param_description": r"^\s*{param_name}:\s*(.+?)(?=\n\s*\w+:|\Z)",
+    "args_marker": r"\n\s*Args:\s*\n",
+    "examples_marker": r"\n\s*Examples:\s*\n",
+    "details_marker": r"\n\s*Details:\s*\n",
+    "category_marker": r"\n\s*Category:\s*\n",
+}
+
+# Output file configuration
+OUTPUT_CONFIG: Dict[str, Union[str, int]] = {
+    "output_dir": "./references",
+    "filename": f"posthog-python-references-{VERSION}.json",
+    "filename_latest": "posthog-python-references-latest.json",
+    "indent": 2,
+}
+
+# Documentation structure defaults
+DOC_DEFAULTS = {
+    "showDocs": True,
+    "releaseTag": "public",
+    "return_type_void": "None",
+    "max_optional_params": 3,
+}

bin/docs_scripts/generate_json_schemas.py

@@ -0,0 +1,498 @@
+#!/usr/bin/env python3
+"""
+Generate comprehensive SDK documentation JSON from PostHog Python SDK.
+This script inspects the code and docstrings to create documentation in the specified format.
+"""
+
+import json
+import inspect
+import re
+from dataclasses import is_dataclass, fields
+from typing import get_origin, get_args, Union
+from textwrap import dedent
+from doc_constant import (
+    DOCUMENTATION_METADATA,
+    DOCSTRING_PATTERNS,
+    OUTPUT_CONFIG,
+    DOC_DEFAULTS,
+)
+import os
+
+
+def extract_examples_from_docstring(docstring: str) -> list:
+    """Extract code examples from docstring."""
+    if not docstring:
+        return []
+
+    examples = []
+
+    # Look for Examples section in the new format
+    examples_section_match = re.search(
+        DOCSTRING_PATTERNS["examples_section"], docstring, re.DOTALL
+    )
+    if examples_section_match:
+        examples_content = examples_section_match.group(1).strip()
+        # Extract code blocks from the Examples section
+        code_blocks = re.findall(
+            DOCSTRING_PATTERNS["code_block"], examples_content, re.DOTALL
+        )
+        for i, code_block in enumerate(code_blocks):
+            # Remove common leading whitespace while preserving relative indentation
+            code = dedent(code_block).strip()
+
+            # Extract name from first comment line if present
+            lines = code.split("\n")
+            name = f"Example {i + 1}"  # Default fallback
+
+            if lines and lines[0].strip().startswith("#"):
+                # Extract name from first comment, keep the comment in the code
+                comment_text = lines[0].strip()[1:].strip()
+                if comment_text:
+                    name = comment_text
+
+            examples.append({"id": f"example_{i + 1}", "name": name, "code": code})
+
+    return examples
+
+
+def extract_details_from_docstring(docstring: str) -> str:
+    """Extract details section from docstring."""
+    if not docstring:
+        return ""
+
+    # Look for Details section
+    details_match = re.search(
+        DOCSTRING_PATTERNS["details_section"], docstring, re.DOTALL
+    )
+    if details_match:
+        details_content = details_match.group(1).strip()
+        # Clean up formatting
+        return details_content.replace("\n", " ")
+
+    return ""
+
+
+def parse_docstring_tags(docstring: str) -> dict:
+    """Parse tags from docstring Category section."""
+    if not docstring:
+        return {}
+
+    tags = {}
+
+    # Extract Category section
+    category_match = re.search(DOCSTRING_PATTERNS["category_section"], docstring)
+    if category_match:
+        category_value = category_match.group(1).strip()
+        tags["category"] = category_value
+
+    return tags
+
+
+def extract_description_from_docstring(docstring: str) -> str:
+    """Extract main description from docstring."""
+    if not docstring:
+        return ""
+
+    # Clean up the docstring
+    cleaned = dedent(docstring).strip()
+
+    # Find the end of the description by looking for first section marker
+    # Check for Args:, Examples:, Details:, or Category: sections
+    section_patterns = [
+        DOCSTRING_PATTERNS["args_marker"],
+        DOCSTRING_PATTERNS["examples_marker"],
+        DOCSTRING_PATTERNS["details_marker"],
+        DOCSTRING_PATTERNS["category_marker"],
+    ]
+
+    end_pos = len(cleaned)
+    for pattern in section_patterns:
+        match = re.search(pattern, cleaned)
+        if match:
+            end_pos = min(end_pos, match.start())
+
+    # Extract description up to the first section marker
+    description = cleaned[:end_pos].strip()
+
+    # Remove one level of \n since it will be rendered as markdown
+    # and \n will be padded in later steps
+    description = description.replace("\n", " ")
+
+    return description
+
+
+def get_type_name(type_annotation) -> str:
+    """Convert type annotation to string name."""
+    if type_annotation is None or type_annotation is type(None):
+        return "any"
+
+    # Handle typing constructs
+    origin = get_origin(type_annotation)
+    if origin is not None:
+        # Handle Union types (including Optional)
+        if origin is Union:
+            args = get_args(type_annotation)
+            if len(args) == 2 and type(None) in args:
+                # This is Optional[Type] - get the non-None type
+                non_none_type = next(arg for arg in args if arg is not type(None))
+                return f"Optional[{get_type_name(non_none_type)}]"
+            else:
+                # Regular Union - list all types
+                type_names = [get_type_name(arg) for arg in args]
+                return f"Union[{', '.join(type_names)}]"
+
+        # Handle other generic types (List, Dict, etc.)
+        origin_name = getattr(origin, "__name__", str(origin))
+        args = get_args(type_annotation)
+        if args:
+            arg_names = [get_type_name(arg) for arg in args]
+            return f"{origin_name}[{', '.join(arg_names)}]"
+        else:
+            return origin_name
+
+    # Handle regular types
+    elif hasattr(type_annotation, "__name__"):
+        return type_annotation.__name__
+    else:
+        return str(type_annotation)
+
+
+def analyze_parameter(param: inspect.Parameter, docstring: str = "") -> dict:
+    """Analyze a function parameter and return its documentation."""
+    # Determine if parameter is optional (has default value)
+    is_optional = param.default == inspect.Parameter.empty
+
+    # Get the type annotation
+    type_annotation = param.annotation
+    param_type = "any"
+
+    if type_annotation != inspect.Parameter.empty:
+        # Handle Union/Optional types first
+        origin = get_origin(type_annotation)
+        if origin is Union:
+            args = get_args(type_annotation)
+            if len(args) == 2 and type(None) in args:
+                # This is Optional[Type]
+                non_none_type = next(arg for arg in args if arg is not type(None))
+                param_type = get_type_name(non_none_type)
+                is_optional = True
+            else:
+                # Other Union types, use first type
+                param_type = get_type_name(args[0]) if args else "any"
+        else:
+            param_type = get_type_name(type_annotation)
+    elif param.default != inspect.Parameter.empty:
+        # No type annotation, but has default value - infer type from default
+        param_type = get_type_name(type(param.default))
+
+    # Extract parameter description from Args section
+    param_description = ""
+    if docstring:
+        # Look for Args section and extract description for this parameter
+        args_section_match = re.search(
+            DOCSTRING_PATTERNS["args_section"], docstring, re.DOTALL
+        )
+        if args_section_match:
+            args_content = args_section_match.group(1)
+            # Look for the parameter description
+            param_pattern = DOCSTRING_PATTERNS["param_description"].format(
+                param_name=re.escape(param.name)
+            )
+            param_match = re.search(
+                param_pattern, args_content, re.MULTILINE | re.DOTALL
+            )
+            if param_match:
+                param_description = param_match.group(1).strip().replace("\n", " ")
+
+    param_info = {
+        "name": param.name,
+        "description": param_description,
+        "isOptional": is_optional,
+        "type": param_type,
+    }
+
+    return param_info
+
+
+def analyze_function(func, name: str) -> dict:
+    """Analyze a function and return its documentation."""
+    try:
+        sig = inspect.signature(func)
+        docstring = inspect.getdoc(func) or ""
+
+        # Skip functions with empty docstrings
+        if not docstring.strip():
+            return {}
+
+        # Extract parameters (excluding 'self')
+        params = []
+        for param_name, param in sig.parameters.items():
+            if param_name != "self":
+                params.append(analyze_parameter(param, docstring))
+
+        # Special handling for constructor
+        display_name = name
+        if name == "__init__":
+            display_name = func.__qualname__.split(".")[0]
+
+        # Parse tags from docstring
+        tags = parse_docstring_tags(docstring)
+
+        category = tags.get("category", None)
+
+        # Extract description
+        description = extract_description_from_docstring(docstring)
+
+        # Skip if no meaningful description
+        if not description.strip():
+            return {}
+
+        # Extract details section (only if it exists)
+        details = extract_details_from_docstring(docstring)
+
+        # Get examples from docstring, do not generate fallback examples
+        examples = extract_examples_from_docstring(docstring)
+        # If no examples, do not include the examples key or set to empty list
+
+        result = {
+            "id": name,
+            "title": display_name,
+            "description": description,
+            "details": details,
+            "category": category,
+            "params": params,
+            "showDocs": DOC_DEFAULTS["showDocs"],
+            "releaseTag": DOC_DEFAULTS["releaseTag"],
+            "returnType": {
+                "id": "return_type",
+                "name": get_type_name(sig.return_annotation)
+                if sig.return_annotation != inspect.Signature.empty
+                else DOC_DEFAULTS["return_type_void"],
+            },
+        }
+        if examples:
+            result["examples"] = examples
+        return result
+    except Exception as e:
+        print(f"Error analyzing function {name}: {e}")
+        return {}
+
+
+def analyze_class(cls) -> dict:
+    """Analyze a class and return its documentation."""
+    class_doc = inspect.getdoc(cls) or f"Class: {cls.__name__}"
+
+    # Get all public methods and constructor
+    functions = []
+    for method_name in dir(cls):
+        if method_name.startswith("_") and method_name != "__init__":
+            continue
+
+        method = getattr(cls, method_name)
+        if callable(method):
+            func_info = analyze_function(method, method_name)
+            if func_info:  # Only add if not None (empty docstring check)
+                functions.append(func_info)
+
+    return {
+        "id": cls.__name__,
+        "title": cls.__name__,
+        "description": extract_description_from_docstring(class_doc),
+        "functions": functions,
+    }
+
+
+def analyze_type(cls) -> dict:
+    """Analyze a type/dataclass and return its documentation."""
+    type_info = {
+        "id": cls.__name__,
+        "name": cls.__name__,
+        "path": f"{cls.__module__}.{cls.__name__}",
+        "properties": [],
+        "example": "",
+    }
+
+    if is_dataclass(cls):
+        # Handle dataclass
+        for field in fields(cls):
+            prop = {
+                "name": field.name,
+                "type": get_type_name(field.type),
+                "description": f"Field: {field.name}",
+            }
+            type_info["properties"].append(prop)
+    elif hasattr(cls, "__annotations__"):
+        # Handle TypedDict or annotated class
+        for field_name, field_type in cls.__annotations__.items():
+            prop = {
+                "name": field_name,
+                "type": get_type_name(field_type),
+                "description": f"Field: {field_name}",
+            }
+            type_info["properties"].append(prop)
+
+    return type_info
+
+
+def generate_sdk_documentation():
+    """Generate complete SDK documentation in the requested format."""
+
+    # Import PostHog components
+    import posthog
+    from posthog.client import Client
+    import posthog.types as types_module
+    import posthog.args as args_module
+    from posthog.version import VERSION
+
+    # Main SDK info
+    sdk_info = {
+        "version": VERSION,
+        "id": "posthog-python",
+        "title": "PostHog Python SDK",
+        "description": "Integrate PostHog into any python application.",
+        "slugPrefix": DOCUMENTATION_METADATA["slugPrefix"],
+        "specUrl": DOCUMENTATION_METADATA["specUrl"],
+    }
+
+    # Collect types
+    types_list = []
+
+    # Types from posthog.types
+    for name in dir(types_module):
+        obj = getattr(types_module, name)
+        if inspect.isclass(obj) and not name.startswith("_"):
+            try:
+                type_info = analyze_type(obj)
+                types_list.append(type_info)
+            except Exception as e:
+                print(f"Error analyzing type {name}: {e}")
+
+    # Types from posthog.args
+    for name in dir(args_module):
+        obj = getattr(args_module, name)
+        if inspect.isclass(obj) and not name.startswith("_"):
+            try:
+                type_info = analyze_type(obj)
+                types_list.append(type_info)
+            except Exception as e:
+                print(f"Error analyzing type {name}: {e}")
+
+    # Clean types of empty types
+
+    # Remove types that have no properties and no examples
+    # Remove types that have no properties and no examples
+    types_list = [
+        t for t in types_list if len(t["properties"]) > 0 or t["example"] != ""
+    ]
+
+    # Collect classes
+    classes_list = []
+
+    # Main PostHog class (renamed from Client)
+    client_class = analyze_class(Client)
+    client_class["id"] = "PostHog"
+    client_class["title"] = "PostHog"
+    classes_list.append(client_class)
+
+    # Global module functions (functions callable as posthog.function_name)
+    global_functions = []
+    for func_name in dir(posthog):
+        # Skip private functions and non-callables
+        if func_name.startswith("_") or not callable(getattr(posthog, func_name)):
+            continue
+
+        func = getattr(posthog, func_name)
+        # Only include functions actually defined in the posthog module (not imported)
+        # and exclude class references
+        if (
+            func_name not in ["Client", "Posthog"]
+            and hasattr(func, "__module__")
+            and func.__module__ == "posthog"
+        ):
+            try:
+                func_info = analyze_function(func, func_name)
+                if func_info:  # Only add if not None (has proper docstring)
+                    global_functions.append(func_info)
+            except Exception:
+                continue
+
+    # Add global functions as a "class"
+    if global_functions:
+        classes_list.append(
+            {
+                "id": "PostHogModule",
+                "title": "PostHog Module Functions",
+                "description": "Global functions available in the PostHog module",
+                "functions": global_functions,
+            }
+        )
+
+    # Collect categories from functions
+    categories = ["Initialization", "Identification", "Capture"]
+    seen_categories = set(categories)
+    for class_info in classes_list:
+        if "functions" in class_info:
+            for func in class_info["functions"]:
+                if (
+                    "category" in func
+                    and func["category"] not in seen_categories
+                    and func["category"]
+                ):
+                    categories.append(func["category"])
+                    seen_categories.add(func["category"])
+
+    # Create the final structure
+    result = {
+        "id": "posthog-python",
+        "hogRef": DOCUMENTATION_METADATA["hogRef"],
+        "info": sdk_info,
+        "types": types_list,
+        "classes": classes_list,
+        "categories": categories,
+    }
+
+    return result
+
+
+if __name__ == "__main__":
+    print("Generating PostHog Python SDK documentation...")
+
+    try:
+        documentation = generate_sdk_documentation()
+
+        # Ensure output directory exists
+        output_dir = str(OUTPUT_CONFIG["output_dir"])
+        os.makedirs(output_dir, exist_ok=True)
+
+        output_file = os.path.join(
+            str(OUTPUT_CONFIG["output_dir"]), str(OUTPUT_CONFIG["filename"])
+        )
+        output_file_latest = os.path.join(
+            str(OUTPUT_CONFIG["output_dir"]), str(OUTPUT_CONFIG["filename_latest"])
+        )
+
+        # Write to current version
+        with open(output_file, "w") as f:
+            json.dump(documentation, f, indent=int(OUTPUT_CONFIG["indent"]))
+        # Write to latest
+        with open(output_file_latest, "w") as f:
+            json.dump(documentation, f, indent=int(OUTPUT_CONFIG["indent"]))
+
+        print(f"✓ Generated {output_file}")
+
+        # Print summary
+        types_count = len(documentation["types"])
+        classes_count = len(documentation["classes"])
+
+        total_functions = sum(len(cls["functions"]) for cls in documentation["classes"])
+
+        print("📊 Documentation Summary:")
+        print(f"   • {types_count} types documented")
+        print(f"   • {classes_count} classes documented")
+        print(f"   • {total_functions} functions documented")
+
+    except Exception as e:
+        print(f"❌ Error generating documentation: {e}")
+        import traceback
+
+        traceback.print_exc()

bin/fmt

@@ -6,9 +6,7 @@ set_source_and_root_dir
 ensure_virtual_env
 
 if [[ "$1" == "--check" ]]; then
-  black --check .
-  isort --check-only .
+  ruff format --check .
 else
-  black .
-  isort .
+  ruff format .
 fi

example.py

@@ -1,107 +1,508 @@
 # PostHog Python library example
-import argparse
+#
+# This script demonstrates various PostHog Python SDK capabilities including:
+# - Basic event capture and user identification
+# - Feature flag local evaluation
+# - Feature flag payloads
+# - Context management and tagging
+#
+# Setup:
+# 1. Copy .env.example to .env and fill in your PostHog credentials
+# 2. Run this script and choose from the interactive menu
+
+import os
 
 import posthog
 
-# Add argument parsing
-parser = argparse.ArgumentParser(description="PostHog Python library example")
-parser.add_argument(
-    "--flag", default="person-on-events-enabled", help="Feature flag key to check (default: person-on-events-enabled)"
-)
-args = parser.parse_args()
 
-posthog.debug = True
+def load_env_file():
+    """Load environment variables from .env file if it exists."""
+    env_path = os.path.join(os.path.dirname(__file__), ".env")
+    if os.path.exists(env_path):
+        with open(env_path, "r") as f:
+            for line in f:
+                line = line.strip()
+                if line and not line.startswith("#") and "=" in line:
+                    key, value = line.split("=", 1)
+                    os.environ.setdefault(key.strip(), value.strip())
 
-# You can find this key on the /setup page in PostHog
-posthog.project_api_key = "phc_gtWmTq3Pgl06u4sZY3TRcoQfp42yfuXHKoe8ZVSR6Kh"
-posthog.personal_api_key = "phx_fiRCOQkTA3o2ePSdLrFDAILLHjMu2Mv52vUi8MNruIm"
 
-# Where you host PostHog, with no trailing /.
-# You can remove this line if you're using posthog.com
-posthog.host = "http://localhost:8000"
+# Load .env file if it exists
+load_env_file()
+
+# Get configuration
+project_key = os.getenv("POSTHOG_PROJECT_API_KEY", "")
+personal_api_key = os.getenv("POSTHOG_PERSONAL_API_KEY", "")
+host = os.getenv("POSTHOG_HOST", "http://localhost:8000")
+
+# Check if project key is provided (required)
+if not project_key:
+    print("❌ Missing PostHog project API key!")
+    print("   Please set POSTHOG_PROJECT_API_KEY environment variable")
+    print("   or copy .env.example to .env and fill in your values")
+    exit(1)
+
+# Configure PostHog with credentials
+posthog.debug = False
+posthog.api_key = project_key
+posthog.project_api_key = project_key
+posthog.host = host
 posthog.poll_interval = 10
 
-print(
-    posthog.feature_enabled(
-        args.flag,  # Use the flag from command line arguments
-        "12345",
-        groups={"organization": str("0182ee91-8ef7-0000-4cb9-fedc5f00926a")},
-        group_properties={
-            "organization": {
-                "id": "0182ee91-8ef7-0000-4cb9-fedc5f00926a",
-                "created_at": "2022-06-30 11:44:52.984121+00:00",
-            }
-        },
+# Check if personal API key is available for local evaluation
+local_eval_available = bool(personal_api_key)
+if personal_api_key:
+    posthog.personal_api_key = personal_api_key
+
+print("🔑 PostHog Configuration:")
+print(f"   Project API Key: {project_key[:9]}...")
+if local_eval_available:
+    print("   Personal API Key: [SET]")
+else:
+    print("   Personal API Key: [NOT SET] - Local evaluation examples will be skipped")
+print(f"   Host: {host}\n")
+
+# Display menu and get user choice
+print("🚀 PostHog Python SDK Demo - Choose an example to run:\n")
+print("1. Identify and capture examples")
+local_eval_note = "" if local_eval_available else " [requires personal API key]"
+print(f"2. Feature flag local evaluation examples{local_eval_note}")
+print("3. Feature flag payload examples")
+print(f"4. Flag dependencies examples{local_eval_note}")
+print("5. Context management and tagging examples")
+print("6. Run all examples")
+print("7. Exit")
+choice = input("\nEnter your choice (1-7): ").strip()
+
+if choice == "1":
+    print("\n" + "=" * 60)
+    print("IDENTIFY AND CAPTURE EXAMPLES")
+    print("=" * 60)
+
+    posthog.debug = True
+
+    # Capture an event
+    print("📊 Capturing events...")
+    posthog.capture(
+        "event",
+        distinct_id="distinct_id",
+        properties={"property1": "value", "property2": "value"},
+        send_feature_flags=True,
+    )
+
+    # Alias a previous distinct id with a new one
+    print("🔗 Creating alias...")
+    posthog.alias("distinct_id", "new_distinct_id")
+
+    posthog.capture(
+        "event2",
+        distinct_id="new_distinct_id",
+        properties={"property1": "value", "property2": "value"},
+    )
+    posthog.capture(
+        "event-with-groups",
+        distinct_id="new_distinct_id",
+        properties={"property1": "value", "property2": "value"},
+        groups={"company": "id:5"},
+    )
+
+    # Add properties to the person
+    print("👤 Identifying user...")
+    posthog.set(
+        distinct_id="new_distinct_id", properties={"email": "something@something.com"}
+    )
+
+    # Add properties to a group
+    print("🏢 Identifying group...")
+    posthog.group_identify("company", "id:5", {"employees": 11})
+
+    # Properties set only once to the person
+    print("🔒 Setting properties once...")
+    posthog.set_once(
+        distinct_id="new_distinct_id", properties={"self_serve_signup": True}
+    )
+
+    # This will not change the property (because it was already set)
+    posthog.set_once(
+        distinct_id="new_distinct_id", properties={"self_serve_signup": False}
+    )
+
+    print("🔄 Updating properties...")
+    posthog.set(distinct_id="new_distinct_id", properties={"current_browser": "Chrome"})
+    posthog.set(
+        distinct_id="new_distinct_id", properties={"current_browser": "Firefox"}
+    )
+
+elif choice == "2":
+    if not local_eval_available:
+        print("\n❌ This example requires a personal API key for local evaluation.")
+        print(
+            "   Set POSTHOG_PERSONAL_API_KEY environment variable to run this example."
+        )
+        posthog.shutdown()
+        exit(1)
+
+    print("\n" + "=" * 60)
+    print("FEATURE FLAG LOCAL EVALUATION EXAMPLES")
+    print("=" * 60)
+
+    posthog.debug = True
+
+    print("🏁 Testing basic feature flags...")
+    print(
+        f"beta-feature for 'distinct_id': {posthog.feature_enabled('beta-feature', 'distinct_id')}"
+    )
+    print(
+        f"beta-feature for 'new_distinct_id': {posthog.feature_enabled('beta-feature', 'new_distinct_id')}"
+    )
+    print(
+        f"beta-feature with groups: {posthog.feature_enabled('beta-feature-groups', 'distinct_id', groups={'company': 'id:5'})}"
+    )
+
+    print("\n🌍 Testing location-based flags...")
+    # Assume test-flag has `City Name = Sydney` as a person property set
+    print(
+        f"Sydney user: {posthog.feature_enabled('test-flag', 'random_id_12345', person_properties={'$geoip_city_name': 'Sydney'})}"
+    )
+
+    print(
+        f"Sydney user (local only): {posthog.feature_enabled('test-flag', 'distinct_id_random_22', person_properties={'$geoip_city_name': 'Sydney'}, only_evaluate_locally=True)}"
+    )
+
+    print("\n📋 Getting all flags...")
+    print(f"All flags: {posthog.get_all_flags('distinct_id_random_22')}")
+    print(
+        f"All flags (local): {posthog.get_all_flags('distinct_id_random_22', only_evaluate_locally=True)}"
+    )
+    print(
+        f"All flags with properties: {posthog.get_all_flags('distinct_id_random_22', person_properties={'$geoip_city_name': 'Sydney'}, only_evaluate_locally=True)}"
+    )
+
+elif choice == "3":
+    print("\n" + "=" * 60)
+    print("FEATURE FLAG PAYLOAD EXAMPLES")
+    print("=" * 60)
+
+    posthog.debug = True
+
+    print("📦 Testing feature flag payloads...")
+    print(
+        f"beta-feature payload: {posthog.get_feature_flag_payload('beta-feature', 'distinct_id')}"
+    )
+    print(
+        f"All flags and payloads: {posthog.get_all_flags_and_payloads('distinct_id')}"
+    )
+    print(
+        f"Remote config payload: {posthog.get_remote_config_payload('encrypted_payload_flag_key')}"
+    )
+
+    # Get feature flag result with all details (enabled, variant, payload, key, reason)
+    print("\n🔍 Getting detailed flag result...")
+    result = posthog.get_feature_flag_result("beta-feature", "distinct_id")
+    if result:
+        print(f"Flag key: {result.key}")
+        print(f"Flag enabled: {result.enabled}")
+        print(f"Variant: {result.variant}")
+        print(f"Payload: {result.payload}")
+        print(f"Reason: {result.reason}")
+        # get_value() returns the variant if it exists, otherwise the enabled value
+        print(f"Value (variant or enabled): {result.get_value()}")
+
+elif choice == "4":
+    if not local_eval_available:
+        print("\n❌ This example requires a personal API key for local evaluation.")
+        print(
+            "   Set POSTHOG_PERSONAL_API_KEY environment variable to run this example."
+        )
+        posthog.shutdown()
+        exit(1)
+
+    print("\n" + "=" * 60)
+    print("FLAG DEPENDENCIES EXAMPLES")
+    print("=" * 60)
+    print("🔗 Testing flag dependencies with local evaluation...")
+    print(
+        "   Flag structure: 'test-flag-dependency' depends on 'beta-feature' being enabled"
+    )
+    print("")
+    print("📋 Required setup (if 'test-flag-dependency' doesn't exist):")
+    print("   1. Create feature flag 'beta-feature':")
+    print("      - Condition: email contains '@example.com'")
+    print("      - Rollout: 100%")
+    print("   2. Create feature flag 'test-flag-dependency':")
+    print("      - Condition: flag 'beta-feature' is enabled")
+    print("      - Rollout: 100%")
+    print("")
+
+    posthog.debug = True
+
+    # Test @example.com user (should satisfy dependency if flags exist)
+    result1 = posthog.feature_enabled(
+        "test-flag-dependency",
+        "example_user",
+        person_properties={"email": "user@example.com"},
         only_evaluate_locally=True,
     )
-)
+    print(f"✅ @example.com user (test-flag-dependency): {result1}")
 
-
-# Capture an event
-posthog.capture("distinct_id", "event", {"property1": "value", "property2": "value"}, send_feature_flags=True)
-
-print(posthog.feature_enabled("beta-feature", "distinct_id"))
-print(posthog.feature_enabled("beta-feature-groups", "distinct_id", groups={"company": "id:5"}))
-
-print(posthog.feature_enabled("beta-feature", "distinct_id"))
-
-# get payload
-print(posthog.get_feature_flag_payload("beta-feature", "distinct_id"))
-print(posthog.get_all_flags_and_payloads("distinct_id"))
-exit()
-# # Alias a previous distinct id with a new one
-
-posthog.alias("distinct_id", "new_distinct_id")
-
-posthog.capture("new_distinct_id", "event2", {"property1": "value", "property2": "value"})
-posthog.capture(
-    "new_distinct_id", "event-with-groups", {"property1": "value", "property2": "value"}, groups={"company": "id:5"}
-)
-
-# # Add properties to the person
-posthog.identify("new_distinct_id", {"email": "something@something.com"})
-
-# Add properties to a group
-posthog.group_identify("company", "id:5", {"employees": 11})
-
-# properties set only once to the person
-posthog.set_once("new_distinct_id", {"self_serve_signup": True})
-
-
-posthog.set_once(
-    "new_distinct_id", {"self_serve_signup": False}
-)  # this will not change the property (because it was already set)
-
-posthog.set("new_distinct_id", {"current_browser": "Chrome"})
-posthog.set("new_distinct_id", {"current_browser": "Firefox"})
-
-
-# #############################################################################
-# Make sure you have a personal API key for the examples below
-
-# Local Evaluation
-
-# If flag has City=Sydney, this call doesn't go to `/decide`
-print(posthog.feature_enabled("test-flag", "distinct_id_random_22", person_properties={"$geoip_city_name": "Sydney"}))
-
-print(
-    posthog.feature_enabled(
-        "test-flag",
-        "distinct_id_random_22",
-        person_properties={"$geoip_city_name": "Sydney"},
+    # Test non-example.com user (dependency should not be satisfied)
+    result2 = posthog.feature_enabled(
+        "test-flag-dependency",
+        "regular_user",
+        person_properties={"email": "user@other.com"},
         only_evaluate_locally=True,
     )
-)
+    print(f"❌ Regular user (test-flag-dependency): {result2}")
 
-
-print(posthog.get_all_flags("distinct_id_random_22"))
-print(posthog.get_all_flags("distinct_id_random_22", only_evaluate_locally=True))
-print(
-    posthog.get_all_flags(
-        "distinct_id_random_22", person_properties={"$geoip_city_name": "Sydney"}, only_evaluate_locally=True
+    # Test beta-feature directly for comparison
+    beta1 = posthog.feature_enabled(
+        "beta-feature",
+        "example_user",
+        person_properties={"email": "user@example.com"},
+        only_evaluate_locally=True,
     )
-)
-print(posthog.get_remote_config_payload("encrypted_payload_flag_key"))
+    beta2 = posthog.feature_enabled(
+        "beta-feature",
+        "regular_user",
+        person_properties={"email": "user@other.com"},
+        only_evaluate_locally=True,
+    )
+    print(f"📊 Beta feature comparison - @example.com: {beta1}, regular: {beta2}")
 
+    print("\n🎯 Results Summary:")
+    print(
+        f"   - Flag dependencies evaluated locally: {'✅ YES' if result1 != result2 else '❌ NO'}"
+    )
+    print("   - Zero API calls needed: ✅ YES (all evaluated locally)")
+    print("   - Python SDK supports flag dependencies: ✅ YES")
+
+    print("\n" + "-" * 60)
+    print("PRODUCTION-STYLE MULTIVARIATE DEPENDENCY CHAIN")
+    print("-" * 60)
+    print("🔗 Testing complex multivariate flag dependencies...")
+    print(
+        "   Structure: multivariate-root-flag -> multivariate-intermediate-flag -> multivariate-leaf-flag"
+    )
+    print("")
+    print("📋 Required setup (if flags don't exist):")
+    print(
+        "   1. Create 'multivariate-leaf-flag' with fruit variants (pineapple, mango, papaya, kiwi)"
+    )
+    print("      - pineapple: email = 'pineapple@example.com'")
+    print("      - mango: email = 'mango@example.com'")
+    print(
+        "   2. Create 'multivariate-intermediate-flag' with color variants (blue, red)"
+    )
+    print("      - blue: depends on multivariate-leaf-flag = 'pineapple'")
+    print("      - red: depends on multivariate-leaf-flag = 'mango'")
+    print(
+        "   3. Create 'multivariate-root-flag' with show variants (breaking-bad, the-wire)"
+    )
+    print("      - breaking-bad: depends on multivariate-intermediate-flag = 'blue'")
+    print("      - the-wire: depends on multivariate-intermediate-flag = 'red'")
+    print("")
+
+    # Test pineapple -> blue -> breaking-bad chain
+    dependent_result3 = posthog.get_feature_flag(
+        "multivariate-root-flag",
+        "regular_user",
+        person_properties={"email": "pineapple@example.com"},
+        only_evaluate_locally=True,
+    )
+    if str(dependent_result3) != "breaking-bad":
+        print(
+            f"     ❌ Something went wrong evaluating 'multivariate-root-flag' with pineapple@example.com. Expected 'breaking-bad', got '{dependent_result3}'"
+        )
+    else:
+        print("✅ 'multivariate-root-flag' with email pineapple@example.com succeeded")
+
+    # Test mango -> red -> the-wire chain
+    dependent_result4 = posthog.get_feature_flag(
+        "multivariate-root-flag",
+        "regular_user",
+        person_properties={"email": "mango@example.com"},
+        only_evaluate_locally=True,
+    )
+    if str(dependent_result4) != "the-wire":
+        print(
+            f"     ❌ Something went wrong evaluating multivariate-root-flag with mango@example.com. Expected 'the-wire', got '{dependent_result4}'"
+        )
+    else:
+        print("✅ 'multivariate-root-flag' with email mango@example.com succeeded")
+
+    # Show the complete chain evaluation
+    print("\n🔍 Complete dependency chain evaluation:")
+    for email, expected_chain in [
+        ("pineapple@example.com", ["pineapple", "blue", "breaking-bad"]),
+        ("mango@example.com", ["mango", "red", "the-wire"]),
+    ]:
+        leaf = posthog.get_feature_flag(
+            "multivariate-leaf-flag",
+            "regular_user",
+            person_properties={"email": email},
+            only_evaluate_locally=True,
+        )
+        intermediate = posthog.get_feature_flag(
+            "multivariate-intermediate-flag",
+            "regular_user",
+            person_properties={"email": email},
+            only_evaluate_locally=True,
+        )
+        root = posthog.get_feature_flag(
+            "multivariate-root-flag",
+            "regular_user",
+            person_properties={"email": email},
+            only_evaluate_locally=True,
+        )
+
+        actual_chain = [str(leaf), str(intermediate), str(root)]
+        chain_success = actual_chain == expected_chain
+
+        print(f"   📧 {email}:")
+        print(f"      Expected: {' -> '.join(map(str, expected_chain))}")
+        print(f"      Actual:   {' -> '.join(map(str, actual_chain))}")
+        print(f"      Status:   {'✅ SUCCESS' if chain_success else '❌ FAILED'}")
+
+    print("\n🎯 Multivariate Chain Summary:")
+    print("   - Complex dependency chains: ✅ SUPPORTED")
+    print("   - Multivariate flag dependencies: ✅ SUPPORTED")
+    print("   - Local evaluation of chains: ✅ WORKING")
+
+elif choice == "5":
+    print("\n" + "=" * 60)
+    print("CONTEXT MANAGEMENT AND TAGGING EXAMPLES")
+    print("=" * 60)
+
+    posthog.debug = True
+
+    print("🏷️ Testing context management...")
+    print(
+        "You can add tags to a context, and these are automatically added to any events captured within that context."
+    )
+
+    # You can enter a new context using a with statement. Any exceptions thrown in the context will be captured,
+    # and tagged with the context tags. Other events captured will also be tagged with the context tags. By default,
+    # the new context inherits tags from the parent context.
+    try:
+        with posthog.new_context():
+            posthog.tag("transaction_id", "abc123")
+            posthog.tag("some_arbitrary_value", {"tags": "can be dicts"})
+
+            # This event will be captured with the tags set above
+            posthog.capture("order_processed")
+            print("✅ Event captured with inherited context tags")
+            # This exception will be captured with the tags set above
+            # raise Exception("Order processing failed")
+    except Exception as e:
+        print(f"Exception captured: {e}")
+
+    # Use fresh=True to start with a clean context (no inherited tags)
+    try:
+        with posthog.new_context(fresh=True):
+            posthog.tag("session_id", "xyz789")
+            # Only session_id tag will be present, no inherited tags
+            posthog.capture("session_event")
+            print("✅ Event captured with fresh context tags")
+            # raise Exception("Session handling failed")
+    except Exception as e:
+        print(f"Exception captured: {e}")
+
+    # You can also use the `@posthog.scoped()` decorator to enter a new context.
+    # By default, it inherits tags from the parent context
+    @posthog.scoped()
+    def process_order(order_id):
+        posthog.tag("order_id", order_id)
+        posthog.capture("order_step_completed")
+        print(f"✅ Order {order_id} processed with scoped context")
+        # Exception will be captured and tagged automatically
+        # raise Exception("Order processing failed")
+
+    # Use fresh=True to start with a clean context (no inherited tags)
+    @posthog.scoped(fresh=True)
+    def process_payment(payment_id):
+        posthog.tag("payment_id", payment_id)
+        posthog.capture("payment_processed")
+        print(f"✅ Payment {payment_id} processed with fresh scoped context")
+        # Only payment_id tag will be present, no inherited tags
+        # raise Exception("Payment processing failed")
+
+    process_order("12345")
+    process_payment("67890")
+
+elif choice == "6":
+    print("\n🔄 Running all examples...")
+    if not local_eval_available:
+        print("   (Skipping local evaluation examples - no personal API key set)\n")
+
+    # Run example 1
+    print(f"\n{'🔸' * 20} IDENTIFY AND CAPTURE {'🔸' * 20}")
+    posthog.debug = True
+    print("📊 Capturing events...")
+    posthog.capture(
+        "event",
+        distinct_id="distinct_id",
+        properties={"property1": "value", "property2": "value"},
+        send_feature_flags=True,
+    )
+    print("🔗 Creating alias...")
+    posthog.alias("distinct_id", "new_distinct_id")
+    print("👤 Identifying user...")
+    posthog.set(
+        distinct_id="new_distinct_id", properties={"email": "something@something.com"}
+    )
+
+    # Run example 2 (requires local evaluation)
+    if local_eval_available:
+        print(f"\n{'🔸' * 20} FEATURE FLAGS {'🔸' * 20}")
+        print("🏁 Testing basic feature flags...")
+        print(f"beta-feature: {posthog.feature_enabled('beta-feature', 'distinct_id')}")
+        print(
+            f"Sydney user: {posthog.feature_enabled('test-flag', 'random_id_12345', person_properties={'$geoip_city_name': 'Sydney'})}"
+        )
+
+    # Run example 3
+    print(f"\n{'🔸' * 20} PAYLOADS {'🔸' * 20}")
+    print("📦 Testing payloads...")
+    print(f"Payload: {posthog.get_feature_flag_payload('beta-feature', 'distinct_id')}")
+
+    # Run example 4 (requires local evaluation)
+    if local_eval_available:
+        print(f"\n{'🔸' * 20} FLAG DEPENDENCIES {'🔸' * 20}")
+        print("🔗 Testing flag dependencies...")
+        result1 = posthog.feature_enabled(
+            "test-flag-dependency",
+            "demo_user",
+            person_properties={"email": "user@example.com"},
+            only_evaluate_locally=True,
+        )
+        result2 = posthog.feature_enabled(
+            "test-flag-dependency",
+            "demo_user2",
+            person_properties={"email": "user@other.com"},
+            only_evaluate_locally=True,
+        )
+        print(f"✅ @example.com user: {result1}, regular user: {result2}")
+
+    # Run example 5
+    print(f"\n{'🔸' * 20} CONTEXT MANAGEMENT {'🔸' * 20}")
+    print("🏷️ Testing context management...")
+    with posthog.new_context():
+        posthog.tag("demo_run", "all_examples")
+        posthog.capture("demo_completed")
+        print("✅ Demo completed with context tags")
+
+elif choice == "7":
+    print("👋 Goodbye!")
+    posthog.shutdown()
+    exit()
+
+else:
+    print("❌ Invalid choice. Please run again and select 1-7.")
+    posthog.shutdown()
+    exit()
+
+print("\n" + "=" * 60)
+print("✅ Example completed!")
+print("=" * 60)
 
 posthog.shutdown()

examples/redis_flag_cache.py

@@ -0,0 +1,144 @@
+"""
+Redis-based distributed cache for PostHog feature flag definitions.
+
+This example demonstrates how to implement a FlagDefinitionCacheProvider
+using Redis for multi-instance deployments (leader election pattern).
+
+Usage:
+    import redis
+    from posthog import Posthog
+
+    redis_client = redis.Redis(host='localhost', port=6379, decode_responses=True)
+    cache = RedisFlagCache(redis_client, service_key="my-service")
+
+    posthog = Posthog(
+        "<project_api_key>",
+        personal_api_key="<personal_api_key>",
+        flag_definition_cache_provider=cache,
+    )
+
+Requirements:
+    pip install redis
+"""
+
+import json
+import uuid
+
+from posthog import FlagDefinitionCacheData, FlagDefinitionCacheProvider
+from redis import Redis
+from typing import Optional
+
+
+class RedisFlagCache(FlagDefinitionCacheProvider):
+    """
+    A distributed cache for PostHog feature flag definitions using Redis.
+
+    In a multi-instance deployment (e.g., multiple serverless functions or containers),
+    we want only ONE instance to poll PostHog for flag updates, while all instances
+    share the cached results. This prevents N instances from making N redundant API calls.
+
+    The implementation uses leader election:
+    - One instance "wins" and becomes responsible for fetching
+    - Other instances read from the shared cache
+    - If the leader dies, the lock expires (TTL) and another instance takes over
+
+    Uses Lua scripts for atomic operations, following Redis distributed lock best practices:
+    https://redis.io/docs/latest/develop/clients/patterns/distributed-locks/
+    """
+
+    LOCK_TTL_MS = 60 * 1000  # 60 seconds, should be longer than the flags poll interval
+    CACHE_TTL_SECONDS = 60 * 60 * 24  # 24 hours
+
+    # Lua script: acquire lock if free, or extend if we own it
+    _LUA_TRY_LEAD = """
+        local current = redis.call('GET', KEYS[1])
+        if current == false then
+            redis.call('SET', KEYS[1], ARGV[1], 'PX', ARGV[2])
+            return 1
+        elseif current == ARGV[1] then
+            redis.call('PEXPIRE', KEYS[1], ARGV[2])
+            return 1
+        end
+        return 0
+    """
+
+    # Lua script: release lock only if we own it
+    _LUA_STOP_LEAD = """
+        if redis.call('GET', KEYS[1]) == ARGV[1] then
+            return redis.call('DEL', KEYS[1])
+        end
+        return 0
+    """
+
+    def __init__(self, redis: Redis[str], service_key: str):
+        """
+        Initialize the Redis flag cache.
+
+        Args:
+            redis: A redis-py client instance. Must be configured with
+                   decode_responses=True for correct string handling.
+            service_key: A unique identifier for this service/environment.
+                         Used to scope Redis keys, allowing multiple services
+                         or environments to share the same Redis instance.
+                         Examples: "my-api-prod", "checkout-service", "staging".
+
+        Redis Keys Created:
+            - posthog:flags:{service_key} - Cached flag definitions (JSON)
+            - posthog:flags:{service_key}:lock - Leader election lock
+
+        Example:
+            redis_client = redis.Redis(
+                host='localhost',
+                port=6379,
+                decode_responses=True
+            )
+            cache = RedisFlagCache(redis_client, service_key="my-api-prod")
+        """
+        self._redis = redis
+        self._cache_key = f"posthog:flags:{service_key}"
+        self._lock_key = f"posthog:flags:{service_key}:lock"
+        self._instance_id = str(uuid.uuid4())
+        self._try_lead = self._redis.register_script(self._LUA_TRY_LEAD)
+        self._stop_lead = self._redis.register_script(self._LUA_STOP_LEAD)
+
+    def get_flag_definitions(self) -> Optional[FlagDefinitionCacheData]:
+        """
+        Retrieve cached flag definitions from Redis.
+
+        Returns:
+            Cached flag definitions if available, None otherwise.
+        """
+        cached = self._redis.get(self._cache_key)
+        return json.loads(cached) if cached else None
+
+    def should_fetch_flag_definitions(self) -> bool:
+        """
+        Determines if this instance should fetch flag definitions from PostHog.
+
+        Atomically either:
+        - Acquires the lock if no one holds it, OR
+        - Extends the lock TTL if we already hold it
+
+        Returns:
+            True if this instance is the leader and should fetch, False otherwise.
+        """
+        result = self._try_lead(
+            keys=[self._lock_key],
+            args=[self._instance_id, self.LOCK_TTL_MS],
+        )
+        return result == 1
+
+    def on_flag_definitions_received(self, data: FlagDefinitionCacheData) -> None:
+        """
+        Store fetched flag definitions in Redis.
+
+        Args:
+            data: The flag definitions to cache.
+        """
+        self._redis.set(self._cache_key, json.dumps(data), ex=self.CACHE_TTL_SECONDS)
+
+    def shutdown(self) -> None:
+        """
+        Release leadership if we hold it. Safe to call even if not the leader.
+        """
+        self._stop_lead(keys=[self._lock_key], args=[self._instance_id])

examples/remote_config.py

@@ -0,0 +1,32 @@
+#!/usr/bin/env python3
+"""
+Simple test script for PostHog remote config endpoint.
+"""
+
+import posthog
+
+# Initialize PostHog client
+posthog.api_key = "phc_..."
+posthog.personal_api_key = "phs_..."  # or "phx_..."
+posthog.host = "http://localhost:8000"  # or "https://us.posthog.com"
+posthog.debug = True
+
+
+def test_remote_config():
+    """Test remote config payload retrieval."""
+    print("Testing remote config endpoint...")
+
+    # Test feature flag key - replace with an actual flag key from your project
+    flag_key = "unencrypted-remote-config-setting"
+
+    try:
+        # Get remote config payload
+        payload = posthog.get_remote_config_payload(flag_key)
+        print(f"✅ Success! Remote config payload for '{flag_key}': {payload}")
+
+    except Exception as e:
+        print(f"❌ Error getting remote config: {e}")
+
+
+if __name__ == "__main__":
+    test_remote_config()

integration_tests/django5/.gitignore

@@ -0,0 +1,4 @@
+db.sqlite3
+*.pyc
+__pycache__/
+.pytest_cache/

integration_tests/django5/manage.py

@@ -1,12 +1,13 @@
 #!/usr/bin/env python
 """Django's command-line utility for administrative tasks."""
+
 import os
 import sys
 
 
 def main():
     """Run administrative tasks."""
-    os.environ.setdefault("DJANGO_SETTINGS_MODULE", "sentry_django_example.settings")
+    os.environ.setdefault("DJANGO_SETTINGS_MODULE", "testdjango.settings")
     try:
         from django.core.management import execute_from_command_line
     except ImportError as exc:

integration_tests/django5/pyproject.toml

@@ -0,0 +1,19 @@
+[project]
+name = "test-django5"
+version = "0.1.0"
+requires-python = ">=3.12"
+dependencies = [
+    "django~=5.2.7",
+    "uvicorn[standard]~=0.38.0",
+    "posthog",
+    "pytest~=8.4.2",
+    "pytest-asyncio~=1.2.0",
+    "pytest-django~=4.11.1",
+    "httpx~=0.28.1",
+]
+
+[tool.uv]
+required-version = ">=0.5"
+
+[tool.uv.sources]
+posthog = { path = "../..", editable = true }

integration_tests/django5/test_exception_capture.py

@@ -0,0 +1,111 @@
+"""
+Test that verifies exception capture functionality.
+
+These tests verify that exceptions are actually captured to PostHog, not just that
+500 responses are returned.
+
+Without process_exception(), view exceptions are NOT captured to PostHog (v6.7.11 and earlier).
+With process_exception(), Django calls this method to capture exceptions before
+converting them to 500 responses.
+"""
+
+import os
+import django
+
+# Setup Django before importing anything else
+os.environ.setdefault("DJANGO_SETTINGS_MODULE", "testdjango.settings")
+django.setup()
+
+import pytest  # noqa: E402
+from httpx import AsyncClient, ASGITransport  # noqa: E402
+from django.core.asgi import get_asgi_application  # noqa: E402
+
+
+@pytest.fixture(scope="session")
+def asgi_app():
+    """Shared ASGI application for all tests."""
+    return get_asgi_application()
+
+
+@pytest.mark.asyncio
+async def test_async_exception_is_captured(asgi_app):
+    """
+    Test that async view exceptions are captured to PostHog.
+
+    The middleware's process_exception() method ensures exceptions are captured.
+    Without it (v6.7.11 and earlier), exceptions are NOT captured even though 500 is returned.
+    """
+    from unittest.mock import patch
+
+    # Track captured exceptions
+    captured = []
+
+    def mock_capture(exception, **kwargs):
+        """Mock capture_exception to record calls."""
+        captured.append(
+            {
+                "exception": exception,
+                "type": type(exception).__name__,
+                "message": str(exception),
+            }
+        )
+
+    # Patch at the posthog module level where middleware imports from
+    with patch("posthog.capture_exception", side_effect=mock_capture):
+        async with AsyncClient(
+            transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+        ) as ac:
+            response = await ac.get("/test/async-exception")
+
+        # Django returns 500
+        assert response.status_code == 500
+
+        # CRITICAL: Verify PostHog captured the exception
+        assert len(captured) > 0, "Exception was NOT captured to PostHog!"
+
+        # Verify it's the right exception
+        exception_data = captured[0]
+        assert exception_data["type"] == "ValueError"
+        assert "Test exception from Django 5 async view" in exception_data["message"]
+
+
+@pytest.mark.asyncio
+async def test_sync_exception_is_captured(asgi_app):
+    """
+    Test that sync view exceptions are captured to PostHog.
+
+    The middleware's process_exception() method ensures exceptions are captured.
+    Without it (v6.7.11 and earlier), exceptions are NOT captured even though 500 is returned.
+    """
+    from unittest.mock import patch
+
+    # Track captured exceptions
+    captured = []
+
+    def mock_capture(exception, **kwargs):
+        """Mock capture_exception to record calls."""
+        captured.append(
+            {
+                "exception": exception,
+                "type": type(exception).__name__,
+                "message": str(exception),
+            }
+        )
+
+    # Patch at the posthog module level where middleware imports from
+    with patch("posthog.capture_exception", side_effect=mock_capture):
+        async with AsyncClient(
+            transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+        ) as ac:
+            response = await ac.get("/test/sync-exception")
+
+        # Django returns 500
+        assert response.status_code == 500
+
+        # CRITICAL: Verify PostHog captured the exception
+        assert len(captured) > 0, "Exception was NOT captured to PostHog!"
+
+        # Verify it's the right exception
+        exception_data = captured[0]
+        assert exception_data["type"] == "ValueError"
+        assert "Test exception from Django 5 sync view" in exception_data["message"]

integration_tests/django5/test_middleware.py

@@ -0,0 +1,170 @@
+"""
+Tests for PostHog Django middleware in async context.
+
+These tests verify that the middleware correctly handles:
+1. Async user access (request.auser() in Django 5)
+2. Exception capture in both sync and async views
+3. No SynchronousOnlyOperation errors in async context
+
+Tests run directly against the ASGI application without needing a server.
+"""
+
+import os
+import django
+
+# Setup Django before importing anything else
+os.environ.setdefault("DJANGO_SETTINGS_MODULE", "testdjango.settings")
+django.setup()
+
+import pytest  # noqa: E402
+from httpx import AsyncClient, ASGITransport  # noqa: E402
+from django.core.asgi import get_asgi_application  # noqa: E402
+
+
+@pytest.fixture(scope="session")
+def asgi_app():
+    """Shared ASGI application for all tests."""
+    return get_asgi_application()
+
+
+@pytest.mark.asyncio
+async def test_async_user_access(asgi_app):
+    """
+    Test that middleware can access request.user in async context.
+
+    In Django 5, this requires using await request.auser() instead of request.user
+    to avoid SynchronousOnlyOperation error.
+
+    Without authentication, request.user is AnonymousUser which doesn't
+    trigger the lazy loading bug. This test verifies the middleware works
+    in the common case.
+    """
+    async with AsyncClient(
+        transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+    ) as ac:
+        response = await ac.get("/test/async-user")
+
+    assert response.status_code == 200
+    data = response.json()
+    assert data["status"] == "success"
+    assert "django_version" in data
+
+
+@pytest.mark.django_db(transaction=True)
+@pytest.mark.asyncio
+async def test_async_authenticated_user_access(asgi_app):
+    """
+    Test that middleware can access an authenticated user in async context.
+
+    This is the critical test that triggers the SynchronousOnlyOperation bug
+    in v6.7.11. When AuthenticationMiddleware sets request.user to a
+    SimpleLazyObject wrapping a database query, accessing user.pk or user.email
+    in async context causes the error.
+
+    In v6.7.11, extract_request_user() does getattr(user, "is_authenticated", False)
+    which triggers the lazy object evaluation synchronously.
+
+    The fix uses await request.auser() instead to avoid this.
+    """
+    from django.contrib.auth import get_user_model
+    from django.test import Client
+    from asgiref.sync import sync_to_async
+    from django.test import override_settings
+
+    # Create a test user (must use sync_to_async since we're in async test)
+    User = get_user_model()
+
+    @sync_to_async
+    def create_or_get_user():
+        user, created = User.objects.get_or_create(
+            username="testuser",
+            defaults={
+                "email": "test@example.com",
+            },
+        )
+        if created:
+            user.set_password("testpass123")
+            user.save()
+        return user
+
+    user = await create_or_get_user()
+
+    # Create a session with authenticated user (sync operation)
+    @sync_to_async
+    def create_session():
+        client = Client()
+        client.force_login(user)
+        return client.cookies.get("sessionid")
+
+    session_cookie = await create_session()
+
+    if not session_cookie:
+        pytest.skip("Could not create authenticated session")
+
+    # Make request with session cookie - this should trigger the bug in v6.7.11
+    # Disable exception capture to see the SynchronousOnlyOperation clearly
+    with override_settings(POSTHOG_MW_CAPTURE_EXCEPTIONS=False):
+        async with AsyncClient(
+            transport=ASGITransport(app=asgi_app),
+            base_url="http://testserver",
+            cookies={"sessionid": session_cookie.value},
+        ) as ac:
+            response = await ac.get("/test/async-user")
+
+        assert response.status_code == 200
+        data = response.json()
+        assert data["status"] == "success"
+        assert data["user_authenticated"]
+
+
+@pytest.mark.asyncio
+async def test_sync_user_access(asgi_app):
+    """
+    Test that middleware works with sync views.
+
+    This should always work regardless of middleware version.
+    """
+    async with AsyncClient(
+        transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+    ) as ac:
+        response = await ac.get("/test/sync-user")
+
+    assert response.status_code == 200
+    data = response.json()
+    assert data["status"] == "success"
+
+
+@pytest.mark.asyncio
+async def test_async_exception_capture(asgi_app):
+    """
+    Test that middleware handles exceptions from async views.
+
+    The middleware's process_exception() method captures view exceptions to PostHog
+    before Django converts them to 500 responses. This test verifies the exception
+    causes a 500 response. See test_exception_capture.py for tests that verify
+    actual exception capture to PostHog.
+    """
+    async with AsyncClient(
+        transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+    ) as ac:
+        response = await ac.get("/test/async-exception")
+
+    # Django returns 500 for unhandled exceptions
+    assert response.status_code == 500
+
+
+@pytest.mark.asyncio
+async def test_sync_exception_capture(asgi_app):
+    """
+    Test that middleware handles exceptions from sync views.
+
+    The middleware's process_exception() method captures view exceptions to PostHog.
+    This test verifies the exception causes a 500 response.
+    """
+    async with AsyncClient(
+        transport=ASGITransport(app=asgi_app), base_url="http://testserver"
+    ) as ac:
+        response = await ac.get("/test/sync-exception")
+
+    # Django returns 500 for unhandled exceptions
+    assert response.status_code == 500

integration_tests/django5/testdjango/asgi.py

@@ -1,16 +1,16 @@
 """
-ASGI config for sentry_django_example project.
+ASGI config for testdjango project.
 
 It exposes the ASGI callable as a module-level variable named ``application``.
 
 For more information on this file, see
-https://docs.djangoproject.com/en/3.2/howto/deployment/asgi/
+https://docs.djangoproject.com/en/5.2/howto/deployment/asgi/
 """
 
 import os
 
 from django.core.asgi import get_asgi_application
 
-os.environ.setdefault("DJANGO_SETTINGS_MODULE", "sentry_django_example.settings")
+os.environ.setdefault("DJANGO_SETTINGS_MODULE", "testdjango.settings")
 
 application = get_asgi_application()

integration_tests/django5/testdjango/settings.py

@@ -0,0 +1,129 @@
+"""
+Django settings for testdjango project.
+
+Generated by 'django-admin startproject' using Django 5.2.7.
+
+For more information on this file, see
+https://docs.djangoproject.com/en/5.2/topics/settings/
+
+For the full list of settings and their values, see
+https://docs.djangoproject.com/en/5.2/ref/settings/
+"""
+
+from pathlib import Path
+
+# Build paths inside the project like this: BASE_DIR / 'subdir'.
+BASE_DIR = Path(__file__).resolve().parent.parent
+
+
+# Quick-start development settings - unsuitable for production
+# See https://docs.djangoproject.com/en/5.2/howto/deployment/checklist/
+
+# SECURITY WARNING: keep the secret key used in production secret!
+SECRET_KEY = "django-insecure-q5(&wfw@_lb)noyowbfl$2ls8c82hl__0f9s5(mohlh2)aas#3"
+
+# SECURITY WARNING: don't run with debug turned on in production!
+DEBUG = True
+
+ALLOWED_HOSTS = ["*"]
+
+
+# Application definition
+
+INSTALLED_APPS = [
+    "django.contrib.admin",
+    "django.contrib.auth",
+    "django.contrib.contenttypes",
+    "django.contrib.sessions",
+    "django.contrib.messages",
+    "django.contrib.staticfiles",
+]
+
+MIDDLEWARE = [
+    "django.middleware.security.SecurityMiddleware",
+    "django.contrib.sessions.middleware.SessionMiddleware",
+    "django.middleware.common.CommonMiddleware",
+    "django.middleware.csrf.CsrfViewMiddleware",
+    "django.contrib.auth.middleware.AuthenticationMiddleware",
+    "django.contrib.messages.middleware.MessageMiddleware",
+    "django.middleware.clickjacking.XFrameOptionsMiddleware",
+    "posthog.integrations.django.PosthogContextMiddleware",  # Test PostHog middleware
+]
+
+ROOT_URLCONF = "testdjango.urls"
+
+TEMPLATES = [
+    {
+        "BACKEND": "django.template.backends.django.DjangoTemplates",
+        "DIRS": [],
+        "APP_DIRS": True,
+        "OPTIONS": {
+            "context_processors": [
+                "django.template.context_processors.request",
+                "django.contrib.auth.context_processors.auth",
+                "django.contrib.messages.context_processors.messages",
+            ],
+        },
+    },
+]
+
+WSGI_APPLICATION = "testdjango.wsgi.application"
+
+
+# Database
+# https://docs.djangoproject.com/en/5.2/ref/settings/#databases
+
+DATABASES = {
+    "default": {
+        "ENGINE": "django.db.backends.sqlite3",
+        "NAME": BASE_DIR / "db.sqlite3",
+    }
+}
+
+
+# Password validation
+# https://docs.djangoproject.com/en/5.2/ref/settings/#auth-password-validators
+
+AUTH_PASSWORD_VALIDATORS = [
+    {
+        "NAME": "django.contrib.auth.password_validation.UserAttributeSimilarityValidator",
+    },
+    {
+        "NAME": "django.contrib.auth.password_validation.MinimumLengthValidator",
+    },
+    {
+        "NAME": "django.contrib.auth.password_validation.CommonPasswordValidator",
+    },
+    {
+        "NAME": "django.contrib.auth.password_validation.NumericPasswordValidator",
+    },
+]
+
+
+# Internationalization
+# https://docs.djangoproject.com/en/5.2/topics/i18n/
+
+LANGUAGE_CODE = "en-us"
+
+TIME_ZONE = "UTC"
+
+USE_I18N = True
+
+USE_TZ = True
+
+
+# Static files (CSS, JavaScript, Images)
+# https://docs.djangoproject.com/en/5.2/howto/static-files/
+
+STATIC_URL = "static/"
+
+# Default primary key field type
+# https://docs.djangoproject.com/en/5.2/ref/settings/#default-auto-field
+
+DEFAULT_AUTO_FIELD = "django.db.models.BigAutoField"
+
+
+# PostHog settings for testing
+POSTHOG_API_KEY = "test-key"
+POSTHOG_HOST = "https://app.posthog.com"
+POSTHOG_MW_CAPTURE_EXCEPTIONS = True

integration_tests/django5/testdjango/urls.py

@@ -1,7 +1,8 @@
-"""sentry_django_example URL Configuration
+"""
+URL configuration for testdjango project.
 
 The `urlpatterns` list routes URLs to views. For more information please see:
-    https://docs.djangoproject.com/en/3.2/topics/http/urls/
+    https://docs.djangoproject.com/en/5.2/topics/http/urls/
 Examples:
 Function views
     1. Add an import:  from my_app import views
@@ -16,13 +17,12 @@ Including another URLconf
 
 from django.contrib import admin
 from django.urls import path
-
-
-def trigger_error(request):
-    division_by_zero = 1 / 0
-
+from testdjango import views
 
 urlpatterns = [
     path("admin/", admin.site.urls),
-    path("sentry-debug/", trigger_error),
+    path("test/async-user", views.test_async_user),
+    path("test/sync-user", views.test_sync_user),
+    path("test/async-exception", views.test_async_exception),
+    path("test/sync-exception", views.test_sync_exception),
 ]

integration_tests/django5/testdjango/views.py

@@ -0,0 +1,50 @@
+"""
+Test views for validating PostHog middleware with Django 5 ASGI.
+"""
+
+from django.http import JsonResponse
+
+
+async def test_async_user(request):
+    """
+    Async view that tests middleware with request.user access.
+
+    The middleware will access request.user (SimpleLazyObject) via auser()
+    in async context. Without the fix, this causes SynchronousOnlyOperation.
+    """
+    # The middleware has already accessed request.user via auser()
+    # If we got here, the fix works!
+    user = await request.auser()
+
+    return JsonResponse(
+        {
+            "status": "success",
+            "message": "Django 5 async middleware test passed!",
+            "django_version": "5.x",
+            "user_authenticated": user.is_authenticated if user else False,
+            "note": "Middleware used await request.auser() successfully",
+        }
+    )
+
+
+def test_sync_user(request):
+    """Sync view for comparison."""
+    return JsonResponse(
+        {
+            "status": "success",
+            "message": "Sync view works",
+            "user_authenticated": request.user.is_authenticated
+            if hasattr(request, "user")
+            else False,
+        }
+    )
+
+
+async def test_async_exception(request):
+    """Async view that raises an exception for testing exception capture."""
+    raise ValueError("Test exception from Django 5 async view")
+
+
+def test_sync_exception(request):
+    """Sync view that raises an exception for testing exception capture."""
+    raise ValueError("Test exception from Django 5 sync view")

integration_tests/django5/testdjango/wsgi.py

@@ -1,16 +1,16 @@
 """
-WSGI config for sentry_django_example project.
+WSGI config for testdjango project.
 
 It exposes the WSGI callable as a module-level variable named ``application``.
 
 For more information on this file, see
-https://docs.djangoproject.com/en/3.2/howto/deployment/wsgi/
+https://docs.djangoproject.com/en/5.2/howto/deployment/wsgi/
 """
 
 import os
 
 from django.core.wsgi import get_wsgi_application
 
-os.environ.setdefault("DJANGO_SETTINGS_MODULE", "sentry_django_example.settings")
+os.environ.setdefault("DJANGO_SETTINGS_MODULE", "testdjango.settings")
 
 application = get_wsgi_application()

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+    { url = "https://files.pythonhosted.org/packages/1b/6c/c65773d6cab416a64d191d6ee8a8b1c68a09970ea6909d16965d26bfed1e/websockets-15.0.1-cp313-cp313-win_amd64.whl", hash = "sha256:e09473f095a819042ecb2ab9465aee615bd9c2028e4ef7d933600a8401c79561", size = 176837, upload-time = "2025-03-05T20:02:55.237Z" },
+    { url = "https://files.pythonhosted.org/packages/fa/a8/5b41e0da817d64113292ab1f8247140aac61cbf6cfd085d6a0fa77f4984f/websockets-15.0.1-py3-none-any.whl", hash = "sha256:f7a866fbc1e97b5c617ee4116daaa09b722101d4a3c170c787450ba409f9736f", size = 169743, upload-time = "2025-03-05T20:03:39.41Z" },
+]

mypy-baseline.txt

@@ -1,7 +1,6 @@
 posthog/utils.py:0: error: Library stubs not installed for "six"  [import-untyped]
 posthog/utils.py:0: error: Library stubs not installed for "dateutil.tz"  [import-untyped]
 posthog/utils.py:0: error: Statement is unreachable  [unreachable]
-posthog/utils.py:0: error: Argument 1 to "join" of "str" has incompatible type "AttributeError"; expected "Iterable[str]"  [arg-type]
 posthog/request.py:0: error: Library stubs not installed for "requests"  [import-untyped]
 posthog/request.py:0: note: Hint: "python3 -m pip install types-requests"
 posthog/request.py:0: error: Library stubs not installed for "dateutil.tz"  [import-untyped]
@@ -23,19 +22,14 @@ posthog/client.py:0: error: Library stubs not installed for "six"  [import-untyp
 posthog/client.py:0: note: Hint: "python3 -m pip install types-six"
 posthog/client.py:0: error: Name "queue" already defined (by an import)  [no-redef]
 posthog/client.py:0: error: Need type annotation for "queue"  [var-annotated]
-posthog/client.py:0: error: Item "None" of "Any | None" has no attribute "get"  [union-attr]
-simulator.py:0: error: Unexpected keyword argument "anonymous_id" for "capture"  [call-arg]
-posthog/__init__.py:0: note: "capture" defined here
-simulator.py:0: error: Unexpected keyword argument "anonymous_id" for "identify"  [call-arg]
-posthog/__init__.py:0: note: "identify" defined here
-simulator.py:0: error: Unexpected keyword argument "traits" for "identify"  [call-arg]
-posthog/__init__.py:0: note: "identify" defined here
-example.py:0: error: Statement is unreachable  [unreachable]
-posthog/sentry/posthog_integration.py:0: error: Statement is unreachable  [unreachable]
-posthog/ai/utils.py:0: error: Need type annotation for "output" (hint: "output: list[<type>] = ...")  [var-annotated]
-posthog/ai/utils.py:0: error: Function "builtins.any" is not valid as a type  [valid-type]
-posthog/ai/utils.py:0: note: Perhaps you meant "typing.Any" instead of "any"?
-posthog/ai/utils.py:0: error: Function "builtins.any" is not valid as a type  [valid-type]
-posthog/ai/utils.py:0: note: Perhaps you meant "typing.Any" instead of "any"?
-sentry_django_example/sentry_django_example/settings.py:0: error: Need type annotation for "ALLOWED_HOSTS" (hint: "ALLOWED_HOSTS: list[<type>] = ...")  [var-annotated]
-sentry_django_example/sentry_django_example/settings.py:0: error: Incompatible types in assignment (expression has type "str", variable has type "None")  [assignment]
+posthog/client.py:0: error: Incompatible types in assignment (expression has type "Any | list[Any]", variable has type "None")  [assignment]
+posthog/client.py:0: error: Incompatible types in assignment (expression has type "dict[Any, Any]", variable has type "None")  [assignment]
+posthog/client.py:0: error: "None" has no attribute "__iter__" (not iterable)  [attr-defined]
+posthog/client.py:0: error: Statement is unreachable  [unreachable]
+posthog/client.py:0: error: Right operand of "and" is never evaluated  [unreachable]
+posthog/client.py:0: error: Incompatible types in assignment (expression has type "Poller", variable has type "None")  [assignment]
+posthog/client.py:0: error: "None" has no attribute "start"  [attr-defined]
+posthog/client.py:0: error: Statement is unreachable  [unreachable]
+posthog/client.py:0: error: Statement is unreachable  [unreachable]
+posthog/client.py:0: error: Name "urlparse" already defined (possibly by an import)  [no-redef]
+posthog/client.py:0: error: Name "parse_qs" already defined (possibly by an import)  [no-redef]

mypy.ini

@@ -9,7 +9,7 @@ check_untyped_defs = True
 warn_unreachable = True
 strict_equality = True
 ignore_missing_imports = True
-exclude = env/.*|venv/.*
+exclude = env/.*|venv/.*|build/.*
 
 [mypy-django.*]
 ignore_missing_imports = True

posthog/ai/anthropic/__init__.py

@@ -1,6 +1,17 @@
 from .anthropic import Anthropic
 from .anthropic_async import AsyncAnthropic
-from .anthropic_providers import AnthropicBedrock, AnthropicVertex, AsyncAnthropicBedrock, AsyncAnthropicVertex
+from .anthropic_providers import (
+    AnthropicBedrock,
+    AnthropicVertex,
+    AsyncAnthropicBedrock,
+    AsyncAnthropicVertex,
+)
+from .anthropic_converter import (
+    format_anthropic_response,
+    format_anthropic_input,
+    extract_anthropic_tools,
+    format_anthropic_streaming_content,
+)
 
 __all__ = [
     "Anthropic",
@@ -9,4 +20,8 @@ __all__ = [
     "AsyncAnthropicBedrock",
     "AnthropicVertex",
     "AsyncAnthropicVertex",
+    "format_anthropic_response",
+    "format_anthropic_input",
+    "extract_anthropic_tools",
+    "format_anthropic_streaming_content",
 ]

posthog/ai/anthropic/anthropic.py

@@ -2,14 +2,29 @@ try:
     import anthropic
     from anthropic.resources import Messages
 except ImportError:
-    raise ModuleNotFoundError("Please install the Anthropic SDK to use this feature: 'pip install anthropic'")
+    raise ModuleNotFoundError(
+        "Please install the Anthropic SDK to use this feature: 'pip install anthropic'"
+    )
 
 import time
 import uuid
-from typing import Any, Dict, Optional
+from typing import Any, Dict, List, Optional
 
-from posthog.ai.utils import call_llm_and_track_usage, get_model_params, merge_system_prompt, with_privacy_mode
+from posthog.ai.types import StreamingContentBlock, TokenUsage, ToolInProgress
+from posthog.ai.utils import (
+    call_llm_and_track_usage,
+    merge_usage_stats,
+)
+from posthog.ai.anthropic.anthropic_converter import (
+    extract_anthropic_usage_from_event,
+    handle_anthropic_content_block_start,
+    handle_anthropic_text_delta,
+    handle_anthropic_tool_delta,
+    finalize_anthropic_tool_input,
+)
+from posthog.ai.sanitization import sanitize_anthropic
 from posthog.client import Client as PostHogClient
+from posthog import setup
 
 
 class Anthropic(anthropic.Anthropic):
@@ -19,14 +34,14 @@ class Anthropic(anthropic.Anthropic):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         """
         Args:
             posthog_client: PostHog client for tracking usage
             **kwargs: Additional arguments passed to the Anthropic client
         """
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = WrappedMessages(self)
 
 
@@ -53,6 +68,7 @@ class WrappedMessages(Messages):
             posthog_groups: Optional group analytics properties
             **kwargs: Arguments passed to Anthropic's messages.create
         """
+
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
@@ -110,35 +126,66 @@ class WrappedMessages(Messages):
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {"input_tokens": 0, "output_tokens": 0}
-        accumulated_content = []
+        usage_stats: TokenUsage = TokenUsage(input_tokens=0, output_tokens=0)
+        accumulated_content = ""
+        content_blocks: List[StreamingContentBlock] = []
+        tools_in_progress: Dict[str, ToolInProgress] = {}
+        current_text_block: Optional[StreamingContentBlock] = None
         response = super().create(**kwargs)
 
         def generator():
             nonlocal usage_stats
-            nonlocal accumulated_content  # noqa: F824
+            nonlocal accumulated_content
+            nonlocal content_blocks
+            nonlocal tools_in_progress
+            nonlocal current_text_block
+
             try:
                 for event in response:
-                    if hasattr(event, "usage") and event.usage:
-                        usage_stats = {
-                            k: getattr(event.usage, k, 0)
-                            for k in [
-                                "input_tokens",
-                                "output_tokens",
-                                "cache_read_input_tokens",
-                                "cache_creation_input_tokens",
-                            ]
-                        }
+                    # Extract usage stats from event
+                    event_usage = extract_anthropic_usage_from_event(event)
+                    merge_usage_stats(usage_stats, event_usage)
 
-                    if hasattr(event, "content") and event.content:
-                        accumulated_content.append(event.content)
+                    # Handle content block start events
+                    if hasattr(event, "type") and event.type == "content_block_start":
+                        block, tool = handle_anthropic_content_block_start(event)
+
+                        if block:
+                            content_blocks.append(block)
+
+                            if block.get("type") == "text":
+                                current_text_block = block
+                            else:
+                                current_text_block = None
+
+                        if tool:
+                            tool_id = tool["block"].get("id")
+                            if tool_id:
+                                tools_in_progress[tool_id] = tool
+
+                    # Handle text delta events
+                    delta_text = handle_anthropic_text_delta(event, current_text_block)
+
+                    if delta_text:
+                        accumulated_content += delta_text
+
+                    # Handle tool input delta events
+                    handle_anthropic_tool_delta(
+                        event, content_blocks, tools_in_progress
+                    )
+
+                    # Handle content block stop events
+                    if hasattr(event, "type") and event.type == "content_block_stop":
+                        current_text_block = None
+                        finalize_anthropic_tool_input(
+                            event, content_blocks, tools_in_progress
+                        )
 
                     yield event
 
             finally:
                 end_time = time.time()
                 latency = end_time - start_time
-                output = "".join(accumulated_content)
 
                 self._capture_streaming_event(
                     posthog_distinct_id,
@@ -149,7 +196,8 @@ class WrappedMessages(Messages):
                     kwargs,
                     usage_stats,
                     latency,
-                    output,
+                    content_blocks,
+                    accumulated_content,
                 )
 
         return generator()
@@ -162,45 +210,39 @@ class WrappedMessages(Messages):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
-        output: str,
+        content_blocks: List[StreamingContentBlock],
+        accumulated_content: str,
     ):
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        from posthog.ai.types import StreamingEventData
+        from posthog.ai.anthropic.anthropic_converter import (
+            format_anthropic_streaming_input,
+            format_anthropic_streaming_output_complete,
+        )
+        from posthog.ai.utils import capture_streaming_event
 
-        event_properties = {
-            "$ai_provider": "anthropic",
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                merge_system_prompt(kwargs, "anthropic"),
+        # Prepare standardized event data
+        formatted_input = format_anthropic_streaming_input(kwargs)
+        sanitized_input = sanitize_anthropic(formatted_input)
+
+        event_data = StreamingEventData(
+            provider="anthropic",
+            model=kwargs.get("model", "unknown"),
+            base_url=str(self._client.base_url),
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_anthropic_streaming_output_complete(
+                content_blocks, accumulated_content
             ),
-            "$ai_output_choices": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                [{"content": output, "role": "assistant"}],
-            ),
-            "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("input_tokens", 0),
-            "$ai_output_tokens": usage_stats.get("output_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
-            "$ai_cache_creation_input_tokens": usage_stats.get("cache_creation_input_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(self._client.base_url),
-            **(posthog_properties or {}),
-        }
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=posthog_distinct_id,
+            trace_id=posthog_trace_id,
+            properties=posthog_properties,
+            privacy_mode=posthog_privacy_mode,
+            groups=posthog_groups,
+        )
 
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
-
-        if hasattr(self._client._ph_client, "capture"):
-            self._client._ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
-            )
+        # Use the common capture function
+        capture_streaming_event(self._client._ph_client, event_data)

posthog/ai/anthropic/anthropic_async.py

@@ -2,13 +2,28 @@ try:
     import anthropic
     from anthropic.resources import AsyncMessages
 except ImportError:
-    raise ModuleNotFoundError("Please install the Anthropic SDK to use this feature: 'pip install anthropic'")
+    raise ModuleNotFoundError(
+        "Please install the Anthropic SDK to use this feature: 'pip install anthropic'"
+    )
 
 import time
 import uuid
-from typing import Any, Dict, Optional
+from typing import Any, Dict, List, Optional
 
-from posthog.ai.utils import call_llm_and_track_usage_async, get_model_params, merge_system_prompt, with_privacy_mode
+from posthog import setup
+from posthog.ai.types import StreamingContentBlock, TokenUsage, ToolInProgress
+from posthog.ai.utils import (
+    call_llm_and_track_usage_async,
+    merge_usage_stats,
+)
+from posthog.ai.anthropic.anthropic_converter import (
+    extract_anthropic_usage_from_event,
+    handle_anthropic_content_block_start,
+    handle_anthropic_text_delta,
+    handle_anthropic_tool_delta,
+    finalize_anthropic_tool_input,
+)
+from posthog.ai.sanitization import sanitize_anthropic
 from posthog.client import Client as PostHogClient
 
 
@@ -19,14 +34,14 @@ class AsyncAnthropic(anthropic.AsyncAnthropic):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         """
         Args:
             posthog_client: PostHog client for tracking usage
             **kwargs: Additional arguments passed to the Anthropic client
         """
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = AsyncWrappedMessages(self)
 
 
@@ -53,6 +68,7 @@ class AsyncWrappedMessages(AsyncMessages):
             posthog_groups: Optional group analytics properties
             **kwargs: Arguments passed to Anthropic's messages.create
         """
+
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
@@ -110,35 +126,66 @@ class AsyncWrappedMessages(AsyncMessages):
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {"input_tokens": 0, "output_tokens": 0}
-        accumulated_content = []
+        usage_stats: TokenUsage = TokenUsage(input_tokens=0, output_tokens=0)
+        accumulated_content = ""
+        content_blocks: List[StreamingContentBlock] = []
+        tools_in_progress: Dict[str, ToolInProgress] = {}
+        current_text_block: Optional[StreamingContentBlock] = None
         response = await super().create(**kwargs)
 
         async def generator():
             nonlocal usage_stats
-            nonlocal accumulated_content  # noqa: F824
+            nonlocal accumulated_content
+            nonlocal content_blocks
+            nonlocal tools_in_progress
+            nonlocal current_text_block
+
             try:
                 async for event in response:
-                    if hasattr(event, "usage") and event.usage:
-                        usage_stats = {
-                            k: getattr(event.usage, k, 0)
-                            for k in [
-                                "input_tokens",
-                                "output_tokens",
-                                "cache_read_input_tokens",
-                                "cache_creation_input_tokens",
-                            ]
-                        }
+                    # Extract usage stats from event
+                    event_usage = extract_anthropic_usage_from_event(event)
+                    merge_usage_stats(usage_stats, event_usage)
 
-                    if hasattr(event, "content") and event.content:
-                        accumulated_content.append(event.content)
+                    # Handle content block start events
+                    if hasattr(event, "type") and event.type == "content_block_start":
+                        block, tool = handle_anthropic_content_block_start(event)
+
+                        if block:
+                            content_blocks.append(block)
+
+                            if block.get("type") == "text":
+                                current_text_block = block
+                            else:
+                                current_text_block = None
+
+                        if tool:
+                            tool_id = tool["block"].get("id")
+                            if tool_id:
+                                tools_in_progress[tool_id] = tool
+
+                    # Handle text delta events
+                    delta_text = handle_anthropic_text_delta(event, current_text_block)
+
+                    if delta_text:
+                        accumulated_content += delta_text
+
+                    # Handle tool input delta events
+                    handle_anthropic_tool_delta(
+                        event, content_blocks, tools_in_progress
+                    )
+
+                    # Handle content block stop events
+                    if hasattr(event, "type") and event.type == "content_block_stop":
+                        current_text_block = None
+                        finalize_anthropic_tool_input(
+                            event, content_blocks, tools_in_progress
+                        )
 
                     yield event
 
             finally:
                 end_time = time.time()
                 latency = end_time - start_time
-                output = "".join(accumulated_content)
 
                 await self._capture_streaming_event(
                     posthog_distinct_id,
@@ -149,7 +196,8 @@ class AsyncWrappedMessages(AsyncMessages):
                     kwargs,
                     usage_stats,
                     latency,
-                    output,
+                    content_blocks,
+                    accumulated_content,
                 )
 
         return generator()
@@ -162,45 +210,39 @@ class AsyncWrappedMessages(AsyncMessages):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
-        output: str,
+        content_blocks: List[StreamingContentBlock],
+        accumulated_content: str,
     ):
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        from posthog.ai.types import StreamingEventData
+        from posthog.ai.anthropic.anthropic_converter import (
+            format_anthropic_streaming_input,
+            format_anthropic_streaming_output_complete,
+        )
+        from posthog.ai.utils import capture_streaming_event
 
-        event_properties = {
-            "$ai_provider": "anthropic",
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                merge_system_prompt(kwargs, "anthropic"),
+        # Prepare standardized event data
+        formatted_input = format_anthropic_streaming_input(kwargs)
+        sanitized_input = sanitize_anthropic(formatted_input)
+
+        event_data = StreamingEventData(
+            provider="anthropic",
+            model=kwargs.get("model", "unknown"),
+            base_url=str(self._client.base_url),
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_anthropic_streaming_output_complete(
+                content_blocks, accumulated_content
             ),
-            "$ai_output_choices": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                [{"content": output, "role": "assistant"}],
-            ),
-            "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("input_tokens", 0),
-            "$ai_output_tokens": usage_stats.get("output_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
-            "$ai_cache_creation_input_tokens": usage_stats.get("cache_creation_input_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(self._client.base_url),
-            **(posthog_properties or {}),
-        }
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=posthog_distinct_id,
+            trace_id=posthog_trace_id,
+            properties=posthog_properties,
+            privacy_mode=posthog_privacy_mode,
+            groups=posthog_groups,
+        )
 
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
-
-        if hasattr(self._client._ph_client, "capture"):
-            self._client._ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
-            )
+        # Use the common capture function
+        capture_streaming_event(self._client._ph_client, event_data)

posthog/ai/anthropic/anthropic_converter.py

@@ -0,0 +1,443 @@
+"""
+Anthropic-specific conversion utilities.
+
+This module handles the conversion of Anthropic API responses and inputs
+into standardized formats for PostHog tracking.
+"""
+
+import json
+from typing import Any, Dict, List, Optional, Tuple
+
+from posthog.ai.types import (
+    FormattedContentItem,
+    FormattedFunctionCall,
+    FormattedMessage,
+    FormattedTextContent,
+    StreamingContentBlock,
+    TokenUsage,
+    ToolInProgress,
+)
+
+
+def format_anthropic_response(response: Any) -> List[FormattedMessage]:
+    """
+    Format an Anthropic response into standardized message format.
+
+    Args:
+        response: The response object from Anthropic API
+
+    Returns:
+        List of formatted messages with role and content
+    """
+
+    output: List[FormattedMessage] = []
+
+    if response is None:
+        return output
+
+    content: List[FormattedContentItem] = []
+
+    # Process content blocks from the response
+    if hasattr(response, "content"):
+        for choice in response.content:
+            if (
+                hasattr(choice, "type")
+                and choice.type == "text"
+                and hasattr(choice, "text")
+                and choice.text
+            ):
+                text_content: FormattedTextContent = {
+                    "type": "text",
+                    "text": choice.text,
+                }
+                content.append(text_content)
+
+            elif (
+                hasattr(choice, "type")
+                and choice.type == "tool_use"
+                and hasattr(choice, "name")
+                and hasattr(choice, "id")
+            ):
+                function_call: FormattedFunctionCall = {
+                    "type": "function",
+                    "id": choice.id,
+                    "function": {
+                        "name": choice.name,
+                        "arguments": getattr(choice, "input", {}),
+                    },
+                }
+                content.append(function_call)
+
+    if content:
+        message: FormattedMessage = {
+            "role": "assistant",
+            "content": content,
+        }
+        output.append(message)
+
+    return output
+
+
+def format_anthropic_input(
+    messages: List[Dict[str, Any]], system: Optional[str] = None
+) -> List[FormattedMessage]:
+    """
+    Format Anthropic input messages with optional system prompt.
+
+    Args:
+        messages: List of message dictionaries
+        system: Optional system prompt to prepend
+
+    Returns:
+        List of formatted messages
+    """
+
+    formatted_messages: List[FormattedMessage] = []
+
+    # Add system message if provided
+    if system is not None:
+        formatted_messages.append({"role": "system", "content": system})
+
+    # Add user messages
+    if messages:
+        for msg in messages:
+            # Messages are already in the correct format, just ensure type safety
+            formatted_msg: FormattedMessage = {
+                "role": msg.get("role", "user"),
+                "content": msg.get("content", ""),
+            }
+            formatted_messages.append(formatted_msg)
+
+    return formatted_messages
+
+
+def extract_anthropic_tools(kwargs: Dict[str, Any]) -> Optional[Any]:
+    """
+    Extract tool definitions from Anthropic API kwargs.
+
+    Args:
+        kwargs: Keyword arguments passed to Anthropic API
+
+    Returns:
+        Tool definitions if present, None otherwise
+    """
+
+    return kwargs.get("tools", None)
+
+
+def format_anthropic_streaming_content(
+    content_blocks: List[StreamingContentBlock],
+) -> List[FormattedContentItem]:
+    """
+    Format content blocks from Anthropic streaming response.
+
+    Used by streaming handlers to format accumulated content blocks.
+
+    Args:
+        content_blocks: List of content block dictionaries from streaming
+
+    Returns:
+        List of formatted content items
+    """
+
+    formatted: List[FormattedContentItem] = []
+
+    for block in content_blocks:
+        if block.get("type") == "text":
+            formatted.append(
+                {
+                    "type": "text",
+                    "text": block.get("text") or "",
+                }
+            )
+
+        elif block.get("type") == "function":
+            formatted.append(
+                {
+                    "type": "function",
+                    "id": block.get("id"),
+                    "function": block.get("function") or {},
+                }
+            )
+
+    return formatted
+
+
+def extract_anthropic_web_search_count(response: Any) -> int:
+    """
+    Extract web search count from Anthropic response.
+
+    Anthropic provides exact web search counts via usage.server_tool_use.web_search_requests.
+
+    Args:
+        response: The response from Anthropic API
+
+    Returns:
+        Number of web search requests (0 if none)
+    """
+    if not hasattr(response, "usage"):
+        return 0
+
+    if not hasattr(response.usage, "server_tool_use"):
+        return 0
+
+    server_tool_use = response.usage.server_tool_use
+
+    if hasattr(server_tool_use, "web_search_requests"):
+        return max(0, int(getattr(server_tool_use, "web_search_requests", 0)))
+
+    return 0
+
+
+def extract_anthropic_usage_from_response(response: Any) -> TokenUsage:
+    """
+    Extract usage from a full Anthropic response (non-streaming).
+
+    Args:
+        response: The complete response from Anthropic API
+
+    Returns:
+        TokenUsage with standardized usage
+    """
+    if not hasattr(response, "usage"):
+        return TokenUsage(input_tokens=0, output_tokens=0)
+
+    result = TokenUsage(
+        input_tokens=getattr(response.usage, "input_tokens", 0),
+        output_tokens=getattr(response.usage, "output_tokens", 0),
+    )
+
+    if hasattr(response.usage, "cache_read_input_tokens"):
+        cache_read = response.usage.cache_read_input_tokens
+        if cache_read and cache_read > 0:
+            result["cache_read_input_tokens"] = cache_read
+
+    if hasattr(response.usage, "cache_creation_input_tokens"):
+        cache_creation = response.usage.cache_creation_input_tokens
+        if cache_creation and cache_creation > 0:
+            result["cache_creation_input_tokens"] = cache_creation
+
+    web_search_count = extract_anthropic_web_search_count(response)
+    if web_search_count > 0:
+        result["web_search_count"] = web_search_count
+
+    return result
+
+
+def extract_anthropic_usage_from_event(event: Any) -> TokenUsage:
+    """
+    Extract usage statistics from an Anthropic streaming event.
+
+    Args:
+        event: Streaming event from Anthropic API
+
+    Returns:
+        Dictionary of usage statistics
+    """
+
+    usage: TokenUsage = TokenUsage()
+
+    # Handle usage stats from message_start event
+    if hasattr(event, "type") and event.type == "message_start":
+        if hasattr(event, "message") and hasattr(event.message, "usage"):
+            usage["input_tokens"] = getattr(event.message.usage, "input_tokens", 0)
+            usage["cache_creation_input_tokens"] = getattr(
+                event.message.usage, "cache_creation_input_tokens", 0
+            )
+            usage["cache_read_input_tokens"] = getattr(
+                event.message.usage, "cache_read_input_tokens", 0
+            )
+
+    # Handle usage stats from message_delta event
+    if hasattr(event, "usage") and event.usage:
+        usage["output_tokens"] = getattr(event.usage, "output_tokens", 0)
+
+        # Extract web search count from usage
+        if hasattr(event.usage, "server_tool_use"):
+            server_tool_use = event.usage.server_tool_use
+            if hasattr(server_tool_use, "web_search_requests"):
+                web_search_count = int(
+                    getattr(server_tool_use, "web_search_requests", 0)
+                )
+                if web_search_count > 0:
+                    usage["web_search_count"] = web_search_count
+
+    return usage
+
+
+def handle_anthropic_content_block_start(
+    event: Any,
+) -> Tuple[Optional[StreamingContentBlock], Optional[ToolInProgress]]:
+    """
+    Handle content block start event from Anthropic streaming.
+
+    Args:
+        event: Content block start event
+
+    Returns:
+        Tuple of (content_block, tool_in_progress)
+    """
+
+    if not (hasattr(event, "type") and event.type == "content_block_start"):
+        return None, None
+
+    if not hasattr(event, "content_block"):
+        return None, None
+
+    block = event.content_block
+
+    if not hasattr(block, "type"):
+        return None, None
+
+    if block.type == "text":
+        content_block: StreamingContentBlock = {"type": "text", "text": ""}
+        return content_block, None
+
+    elif block.type == "tool_use":
+        tool_block: StreamingContentBlock = {
+            "type": "function",
+            "id": getattr(block, "id", ""),
+            "function": {"name": getattr(block, "name", ""), "arguments": {}},
+        }
+        tool_in_progress: ToolInProgress = {"block": tool_block, "input_string": ""}
+        return tool_block, tool_in_progress
+
+    return None, None
+
+
+def handle_anthropic_text_delta(
+    event: Any, current_block: Optional[StreamingContentBlock]
+) -> Optional[str]:
+    """
+    Handle text delta event from Anthropic streaming.
+
+    Args:
+        event: Delta event
+        current_block: Current text block being accumulated
+
+    Returns:
+        Text delta if present
+    """
+
+    if hasattr(event, "delta") and hasattr(event.delta, "text"):
+        delta_text = event.delta.text or ""
+
+        if current_block is not None and current_block.get("type") == "text":
+            text_val = current_block.get("text")
+            if text_val is not None:
+                current_block["text"] = text_val + delta_text
+            else:
+                current_block["text"] = delta_text
+
+        return delta_text
+
+    return None
+
+
+def handle_anthropic_tool_delta(
+    event: Any,
+    content_blocks: List[StreamingContentBlock],
+    tools_in_progress: Dict[str, ToolInProgress],
+) -> None:
+    """
+    Handle tool input delta event from Anthropic streaming.
+
+    Args:
+        event: Tool delta event
+        content_blocks: List of content blocks
+        tools_in_progress: Dictionary tracking tools being accumulated
+    """
+
+    if not (hasattr(event, "type") and event.type == "content_block_delta"):
+        return
+
+    if not (
+        hasattr(event, "delta")
+        and hasattr(event.delta, "type")
+        and event.delta.type == "input_json_delta"
+    ):
+        return
+
+    if hasattr(event, "index") and event.index < len(content_blocks):
+        block = content_blocks[event.index]
+
+        if block.get("type") == "function" and block.get("id") in tools_in_progress:
+            tool = tools_in_progress[block["id"]]
+            partial_json = getattr(event.delta, "partial_json", "")
+            tool["input_string"] += partial_json
+
+
+def finalize_anthropic_tool_input(
+    event: Any,
+    content_blocks: List[StreamingContentBlock],
+    tools_in_progress: Dict[str, ToolInProgress],
+) -> None:
+    """
+    Finalize tool input when content block stops.
+
+    Args:
+        event: Content block stop event
+        content_blocks: List of content blocks
+        tools_in_progress: Dictionary tracking tools being accumulated
+    """
+
+    if not (hasattr(event, "type") and event.type == "content_block_stop"):
+        return
+
+    if hasattr(event, "index") and event.index < len(content_blocks):
+        block = content_blocks[event.index]
+
+        if block.get("type") == "function" and block.get("id") in tools_in_progress:
+            tool = tools_in_progress[block["id"]]
+
+            try:
+                block["function"]["arguments"] = json.loads(tool["input_string"])
+            except (json.JSONDecodeError, Exception):
+                # Keep empty dict if parsing fails
+                pass
+
+            del tools_in_progress[block["id"]]
+
+
+def format_anthropic_streaming_input(kwargs: Dict[str, Any]) -> Any:
+    """
+    Format Anthropic streaming input using system prompt merging.
+
+    Args:
+        kwargs: Keyword arguments passed to Anthropic API
+
+    Returns:
+        Formatted input ready for PostHog tracking
+    """
+    from posthog.ai.utils import merge_system_prompt
+
+    return merge_system_prompt(kwargs, "anthropic")
+
+
+def format_anthropic_streaming_output_complete(
+    content_blocks: List[StreamingContentBlock], accumulated_content: str
+) -> List[FormattedMessage]:
+    """
+    Format complete Anthropic streaming output.
+
+    Combines existing logic for formatting content blocks with fallback to accumulated content.
+
+    Args:
+        content_blocks: List of content blocks accumulated during streaming
+        accumulated_content: Raw accumulated text content as fallback
+
+    Returns:
+        Formatted messages ready for PostHog tracking
+    """
+    formatted_content = format_anthropic_streaming_content(content_blocks)
+
+    if formatted_content:
+        return [{"role": "assistant", "content": formatted_content}]
+    else:
+        # Fallback to accumulated content if no blocks
+        return [
+            {
+                "role": "assistant",
+                "content": [{"type": "text", "text": accumulated_content}],
+            }
+        ]

posthog/ai/anthropic/anthropic_providers.py

@@ -1,11 +1,16 @@
 try:
     import anthropic
 except ImportError:
-    raise ModuleNotFoundError("Please install the Anthropic SDK to use this feature: 'pip install anthropic'")
+    raise ModuleNotFoundError(
+        "Please install the Anthropic SDK to use this feature: 'pip install anthropic'"
+    )
+
+from typing import Optional
 
 from posthog.ai.anthropic.anthropic import WrappedMessages
 from posthog.ai.anthropic.anthropic_async import AsyncWrappedMessages
 from posthog.client import Client as PostHogClient
+from posthog import setup
 
 
 class AnthropicBedrock(anthropic.AnthropicBedrock):
@@ -15,9 +20,9 @@ class AnthropicBedrock(anthropic.AnthropicBedrock):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = WrappedMessages(self)
 
 
@@ -28,9 +33,9 @@ class AsyncAnthropicBedrock(anthropic.AsyncAnthropicBedrock):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = AsyncWrappedMessages(self)
 
 
@@ -41,9 +46,9 @@ class AnthropicVertex(anthropic.AnthropicVertex):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = WrappedMessages(self)
 
 
@@ -54,7 +59,7 @@ class AsyncAnthropicVertex(anthropic.AsyncAnthropicVertex):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
+        self._ph_client = posthog_client or setup()
         self.messages = AsyncWrappedMessages(self)

posthog/ai/gemini/__init__.py

@@ -0,0 +1,25 @@
+from .gemini import Client
+from .gemini_async import AsyncClient
+from .gemini_converter import (
+    format_gemini_input,
+    format_gemini_response,
+    extract_gemini_tools,
+)
+
+
+# Create a genai-like module for perfect drop-in replacement
+class _GenAI:
+    Client = Client
+    AsyncClient = AsyncClient
+
+
+genai = _GenAI()
+
+__all__ = [
+    "Client",
+    "AsyncClient",
+    "genai",
+    "format_gemini_input",
+    "format_gemini_response",
+    "extract_gemini_tools",
+]

posthog/ai/gemini/gemini.py

@@ -0,0 +1,420 @@
+import os
+import time
+import uuid
+from typing import Any, Dict, Optional
+
+from posthog.ai.types import TokenUsage, StreamingEventData
+from posthog.ai.utils import merge_system_prompt
+
+try:
+    from google import genai
+except ImportError:
+    raise ModuleNotFoundError(
+        "Please install the Google Gemini SDK to use this feature: 'pip install google-genai'"
+    )
+
+from posthog import setup
+from posthog.ai.utils import (
+    call_llm_and_track_usage,
+    capture_streaming_event,
+    merge_usage_stats,
+)
+from posthog.ai.gemini.gemini_converter import (
+    extract_gemini_usage_from_chunk,
+    extract_gemini_content_from_chunk,
+    format_gemini_streaming_output,
+)
+from posthog.ai.sanitization import sanitize_gemini
+from posthog.client import Client as PostHogClient
+
+
+class Client:
+    """
+    A drop-in replacement for genai.Client that automatically sends LLM usage events to PostHog.
+
+    Usage:
+        client = Client(
+            api_key="your_api_key",
+            posthog_client=posthog_client,
+            posthog_distinct_id="default_user",  # Optional defaults
+            posthog_properties={"team": "ai"}    # Optional defaults
+        )
+        response = client.models.generate_content(
+            model="gemini-2.0-flash",
+            contents=["Hello world"],
+            posthog_distinct_id="specific_user"  # Override default
+        )
+    """
+
+    _ph_client: PostHogClient
+
+    def __init__(
+        self,
+        api_key: Optional[str] = None,
+        vertexai: Optional[bool] = None,
+        credentials: Optional[Any] = None,
+        project: Optional[str] = None,
+        location: Optional[str] = None,
+        debug_config: Optional[Any] = None,
+        http_options: Optional[Any] = None,
+        posthog_client: Optional[PostHogClient] = None,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs,
+    ):
+        """
+        Args:
+            api_key: Google AI API key. If not provided, will use GOOGLE_API_KEY or API_KEY environment variable (not required for Vertex AI)
+            vertexai: Whether to use Vertex AI authentication
+            credentials: Vertex AI credentials object
+            project: GCP project ID for Vertex AI
+            location: GCP location for Vertex AI
+            debug_config: Debug configuration for the client
+            http_options: HTTP options for the client
+            posthog_client: PostHog client for tracking usage
+            posthog_distinct_id: Default distinct ID for all calls (can be overridden per call)
+            posthog_properties: Default properties for all calls (can be overridden per call)
+            posthog_privacy_mode: Default privacy mode for all calls (can be overridden per call)
+            posthog_groups: Default groups for all calls (can be overridden per call)
+            **kwargs: Additional arguments (for future compatibility)
+        """
+
+        self._ph_client = posthog_client or setup()
+
+        if self._ph_client is None:
+            raise ValueError("posthog_client is required for PostHog tracking")
+
+        self.models = Models(
+            api_key=api_key,
+            vertexai=vertexai,
+            credentials=credentials,
+            project=project,
+            location=location,
+            debug_config=debug_config,
+            http_options=http_options,
+            posthog_client=self._ph_client,
+            posthog_distinct_id=posthog_distinct_id,
+            posthog_properties=posthog_properties,
+            posthog_privacy_mode=posthog_privacy_mode,
+            posthog_groups=posthog_groups,
+            **kwargs,
+        )
+
+
+class Models:
+    """
+    Models interface that mimics genai.Client().models with PostHog tracking.
+    """
+
+    _ph_client: PostHogClient  # Not None after __init__ validation
+
+    def __init__(
+        self,
+        api_key: Optional[str] = None,
+        vertexai: Optional[bool] = None,
+        credentials: Optional[Any] = None,
+        project: Optional[str] = None,
+        location: Optional[str] = None,
+        debug_config: Optional[Any] = None,
+        http_options: Optional[Any] = None,
+        posthog_client: Optional[PostHogClient] = None,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs,
+    ):
+        """
+        Args:
+            api_key: Google AI API key. If not provided, will use GOOGLE_API_KEY or API_KEY environment variable (not required for Vertex AI)
+            vertexai: Whether to use Vertex AI authentication
+            credentials: Vertex AI credentials object
+            project: GCP project ID for Vertex AI
+            location: GCP location for Vertex AI
+            debug_config: Debug configuration for the client
+            http_options: HTTP options for the client
+            posthog_client: PostHog client for tracking usage
+            posthog_distinct_id: Default distinct ID for all calls
+            posthog_properties: Default properties for all calls
+            posthog_privacy_mode: Default privacy mode for all calls
+            posthog_groups: Default groups for all calls
+            **kwargs: Additional arguments (for future compatibility)
+        """
+
+        self._ph_client = posthog_client or setup()
+
+        if self._ph_client is None:
+            raise ValueError("posthog_client is required for PostHog tracking")
+
+        # Store default PostHog settings
+        self._default_distinct_id = posthog_distinct_id
+        self._default_properties = posthog_properties or {}
+        self._default_privacy_mode = posthog_privacy_mode
+        self._default_groups = posthog_groups
+
+        # Build genai.Client arguments
+        client_args: Dict[str, Any] = {}
+
+        # Add Vertex AI parameters if provided
+        if vertexai is not None:
+            client_args["vertexai"] = vertexai
+
+        if credentials is not None:
+            client_args["credentials"] = credentials
+
+        if project is not None:
+            client_args["project"] = project
+
+        if location is not None:
+            client_args["location"] = location
+
+        if debug_config is not None:
+            client_args["debug_config"] = debug_config
+
+        if http_options is not None:
+            client_args["http_options"] = http_options
+
+        # Handle API key authentication
+        if vertexai:
+            # For Vertex AI, api_key is optional
+            if api_key is not None:
+                client_args["api_key"] = api_key
+        else:
+            # For non-Vertex AI mode, api_key is required (backwards compatibility)
+            if api_key is None:
+                api_key = os.environ.get("GOOGLE_API_KEY") or os.environ.get("API_KEY")
+
+            if api_key is None:
+                raise ValueError(
+                    "API key must be provided either as parameter or via GOOGLE_API_KEY/API_KEY environment variable"
+                )
+
+            client_args["api_key"] = api_key
+
+        self._client = genai.Client(**client_args)
+        self._base_url = "https://generativelanguage.googleapis.com"
+
+    def _merge_posthog_params(
+        self,
+        call_distinct_id: Optional[str],
+        call_trace_id: Optional[str],
+        call_properties: Optional[Dict[str, Any]],
+        call_privacy_mode: Optional[bool],
+        call_groups: Optional[Dict[str, Any]],
+    ):
+        """Merge call-level PostHog parameters with client defaults."""
+
+        # Use call-level values if provided, otherwise fall back to defaults
+        distinct_id = (
+            call_distinct_id
+            if call_distinct_id is not None
+            else self._default_distinct_id
+        )
+        privacy_mode = (
+            call_privacy_mode
+            if call_privacy_mode is not None
+            else self._default_privacy_mode
+        )
+        groups = call_groups if call_groups is not None else self._default_groups
+
+        # Merge properties: default properties + call properties (call properties override)
+        properties = dict(self._default_properties)
+
+        if call_properties:
+            properties.update(call_properties)
+
+        if call_trace_id is None:
+            call_trace_id = str(uuid.uuid4())
+
+        return distinct_id, call_trace_id, properties, privacy_mode, groups
+
+    def generate_content(
+        self,
+        model: str,
+        contents,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: Optional[bool] = None,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        """
+        Generate content using Gemini's API while tracking usage in PostHog.
+
+        This method signature exactly matches genai.Client().models.generate_content()
+        with additional PostHog tracking parameters.
+
+        Args:
+            model: The model to use (e.g., 'gemini-2.0-flash')
+            contents: The input content for generation
+            posthog_distinct_id: ID to associate with the usage event (overrides client default)
+            posthog_trace_id: Trace UUID for linking events (auto-generated if not provided)
+            posthog_properties: Extra properties to include in the event (merged with client defaults)
+            posthog_privacy_mode: Whether to redact sensitive information (overrides client default)
+            posthog_groups: Group analytics properties (overrides client default)
+            **kwargs: Arguments passed to Gemini's generate_content
+        """
+
+        # Merge PostHog parameters
+        distinct_id, trace_id, properties, privacy_mode, groups = (
+            self._merge_posthog_params(
+                posthog_distinct_id,
+                posthog_trace_id,
+                posthog_properties,
+                posthog_privacy_mode,
+                posthog_groups,
+            )
+        )
+
+        kwargs_with_contents = {"model": model, "contents": contents, **kwargs}
+
+        return call_llm_and_track_usage(
+            distinct_id,
+            self._ph_client,
+            "gemini",
+            trace_id,
+            properties,
+            privacy_mode,
+            groups,
+            self._base_url,
+            self._client.models.generate_content,
+            **kwargs_with_contents,
+        )
+
+    def _generate_content_streaming(
+        self,
+        model: str,
+        contents,
+        distinct_id: Optional[str],
+        trace_id: Optional[str],
+        properties: Optional[Dict[str, Any]],
+        privacy_mode: bool,
+        groups: Optional[Dict[str, Any]],
+        **kwargs: Any,
+    ):
+        start_time = time.time()
+        usage_stats: TokenUsage = TokenUsage(input_tokens=0, output_tokens=0)
+        accumulated_content = []
+
+        kwargs_without_stream = {"model": model, "contents": contents, **kwargs}
+        response = self._client.models.generate_content_stream(**kwargs_without_stream)
+
+        def generator():
+            nonlocal usage_stats
+            nonlocal accumulated_content
+            try:
+                for chunk in response:
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_gemini_usage_from_chunk(chunk)
+
+                    if chunk_usage:
+                        # Gemini reports cumulative totals, not incremental values
+                        merge_usage_stats(usage_stats, chunk_usage, mode="cumulative")
+
+                    # Extract content from chunk (now returns content blocks)
+                    content_block = extract_gemini_content_from_chunk(chunk)
+
+                    if content_block is not None:
+                        accumulated_content.append(content_block)
+
+                    yield chunk
+
+            finally:
+                end_time = time.time()
+                latency = end_time - start_time
+
+                self._capture_streaming_event(
+                    model,
+                    contents,
+                    distinct_id,
+                    trace_id,
+                    properties,
+                    privacy_mode,
+                    groups,
+                    kwargs,
+                    usage_stats,
+                    latency,
+                    accumulated_content,
+                )
+
+        return generator()
+
+    def _capture_streaming_event(
+        self,
+        model: str,
+        contents,
+        distinct_id: Optional[str],
+        trace_id: Optional[str],
+        properties: Optional[Dict[str, Any]],
+        privacy_mode: bool,
+        groups: Optional[Dict[str, Any]],
+        kwargs: Dict[str, Any],
+        usage_stats: TokenUsage,
+        latency: float,
+        output: Any,
+    ):
+        # Prepare standardized event data
+        formatted_input = self._format_input(contents, **kwargs)
+        sanitized_input = sanitize_gemini(formatted_input)
+
+        event_data = StreamingEventData(
+            provider="gemini",
+            model=model,
+            base_url=self._base_url,
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_gemini_streaming_output(output),
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=distinct_id,
+            trace_id=trace_id,
+            properties=properties,
+            privacy_mode=privacy_mode,
+            groups=groups,
+        )
+
+        # Use the common capture function
+        capture_streaming_event(self._ph_client, event_data)
+
+    def _format_input(self, contents, **kwargs):
+        """Format input contents for PostHog tracking"""
+
+        # Create kwargs dict with contents for merge_system_prompt
+        input_kwargs = {"contents": contents, **kwargs}
+        return merge_system_prompt(input_kwargs, "gemini")
+
+    def generate_content_stream(
+        self,
+        model: str,
+        contents,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: Optional[bool] = None,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        # Merge PostHog parameters
+        distinct_id, trace_id, properties, privacy_mode, groups = (
+            self._merge_posthog_params(
+                posthog_distinct_id,
+                posthog_trace_id,
+                posthog_properties,
+                posthog_privacy_mode,
+                posthog_groups,
+            )
+        )
+
+        return self._generate_content_streaming(
+            model,
+            contents,
+            distinct_id,
+            trace_id,
+            properties,
+            privacy_mode,
+            groups,
+            **kwargs,
+        )

posthog/ai/gemini/gemini_async.py

@@ -0,0 +1,423 @@
+import os
+import time
+import uuid
+from typing import Any, Dict, Optional
+
+from posthog.ai.types import TokenUsage, StreamingEventData
+from posthog.ai.utils import merge_system_prompt
+
+try:
+    from google import genai
+except ImportError:
+    raise ModuleNotFoundError(
+        "Please install the Google Gemini SDK to use this feature: 'pip install google-genai'"
+    )
+
+from posthog import setup
+from posthog.ai.utils import (
+    call_llm_and_track_usage_async,
+    capture_streaming_event,
+    merge_usage_stats,
+)
+from posthog.ai.gemini.gemini_converter import (
+    extract_gemini_usage_from_chunk,
+    extract_gemini_content_from_chunk,
+    format_gemini_streaming_output,
+)
+from posthog.ai.sanitization import sanitize_gemini
+from posthog.client import Client as PostHogClient
+
+
+class AsyncClient:
+    """
+    An async drop-in replacement for genai.Client that automatically sends LLM usage events to PostHog.
+
+    Usage:
+        client = AsyncClient(
+            api_key="your_api_key",
+            posthog_client=posthog_client,
+            posthog_distinct_id="default_user",  # Optional defaults
+            posthog_properties={"team": "ai"}    # Optional defaults
+        )
+        response = await client.models.generate_content(
+            model="gemini-2.0-flash",
+            contents=["Hello world"],
+            posthog_distinct_id="specific_user"  # Override default
+        )
+    """
+
+    _ph_client: PostHogClient
+
+    def __init__(
+        self,
+        api_key: Optional[str] = None,
+        vertexai: Optional[bool] = None,
+        credentials: Optional[Any] = None,
+        project: Optional[str] = None,
+        location: Optional[str] = None,
+        debug_config: Optional[Any] = None,
+        http_options: Optional[Any] = None,
+        posthog_client: Optional[PostHogClient] = None,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs,
+    ):
+        """
+        Args:
+            api_key: Google AI API key. If not provided, will use GOOGLE_API_KEY or API_KEY environment variable (not required for Vertex AI)
+            vertexai: Whether to use Vertex AI authentication
+            credentials: Vertex AI credentials object
+            project: GCP project ID for Vertex AI
+            location: GCP location for Vertex AI
+            debug_config: Debug configuration for the client
+            http_options: HTTP options for the client
+            posthog_client: PostHog client for tracking usage
+            posthog_distinct_id: Default distinct ID for all calls (can be overridden per call)
+            posthog_properties: Default properties for all calls (can be overridden per call)
+            posthog_privacy_mode: Default privacy mode for all calls (can be overridden per call)
+            posthog_groups: Default groups for all calls (can be overridden per call)
+            **kwargs: Additional arguments (for future compatibility)
+        """
+
+        self._ph_client = posthog_client or setup()
+
+        if self._ph_client is None:
+            raise ValueError("posthog_client is required for PostHog tracking")
+
+        self.models = AsyncModels(
+            api_key=api_key,
+            vertexai=vertexai,
+            credentials=credentials,
+            project=project,
+            location=location,
+            debug_config=debug_config,
+            http_options=http_options,
+            posthog_client=self._ph_client,
+            posthog_distinct_id=posthog_distinct_id,
+            posthog_properties=posthog_properties,
+            posthog_privacy_mode=posthog_privacy_mode,
+            posthog_groups=posthog_groups,
+            **kwargs,
+        )
+
+
+class AsyncModels:
+    """
+    Async Models interface that mimics genai.Client().aio.models with PostHog tracking.
+    """
+
+    _ph_client: PostHogClient  # Not None after __init__ validation
+
+    def __init__(
+        self,
+        api_key: Optional[str] = None,
+        vertexai: Optional[bool] = None,
+        credentials: Optional[Any] = None,
+        project: Optional[str] = None,
+        location: Optional[str] = None,
+        debug_config: Optional[Any] = None,
+        http_options: Optional[Any] = None,
+        posthog_client: Optional[PostHogClient] = None,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs,
+    ):
+        """
+        Args:
+            api_key: Google AI API key. If not provided, will use GOOGLE_API_KEY or API_KEY environment variable (not required for Vertex AI)
+            vertexai: Whether to use Vertex AI authentication
+            credentials: Vertex AI credentials object
+            project: GCP project ID for Vertex AI
+            location: GCP location for Vertex AI
+            debug_config: Debug configuration for the client
+            http_options: HTTP options for the client
+            posthog_client: PostHog client for tracking usage
+            posthog_distinct_id: Default distinct ID for all calls
+            posthog_properties: Default properties for all calls
+            posthog_privacy_mode: Default privacy mode for all calls
+            posthog_groups: Default groups for all calls
+            **kwargs: Additional arguments (for future compatibility)
+        """
+
+        self._ph_client = posthog_client or setup()
+
+        if self._ph_client is None:
+            raise ValueError("posthog_client is required for PostHog tracking")
+
+        # Store default PostHog settings
+        self._default_distinct_id = posthog_distinct_id
+        self._default_properties = posthog_properties or {}
+        self._default_privacy_mode = posthog_privacy_mode
+        self._default_groups = posthog_groups
+
+        # Build genai.Client arguments
+        client_args: Dict[str, Any] = {}
+
+        # Add Vertex AI parameters if provided
+        if vertexai is not None:
+            client_args["vertexai"] = vertexai
+
+        if credentials is not None:
+            client_args["credentials"] = credentials
+
+        if project is not None:
+            client_args["project"] = project
+
+        if location is not None:
+            client_args["location"] = location
+
+        if debug_config is not None:
+            client_args["debug_config"] = debug_config
+
+        if http_options is not None:
+            client_args["http_options"] = http_options
+
+        # Handle API key authentication
+        if vertexai:
+            # For Vertex AI, api_key is optional
+            if api_key is not None:
+                client_args["api_key"] = api_key
+        else:
+            # For non-Vertex AI mode, api_key is required (backwards compatibility)
+            if api_key is None:
+                api_key = os.environ.get("GOOGLE_API_KEY") or os.environ.get("API_KEY")
+
+            if api_key is None:
+                raise ValueError(
+                    "API key must be provided either as parameter or via GOOGLE_API_KEY/API_KEY environment variable"
+                )
+
+            client_args["api_key"] = api_key
+
+        self._client = genai.Client(**client_args)
+        self._base_url = "https://generativelanguage.googleapis.com"
+
+    def _merge_posthog_params(
+        self,
+        call_distinct_id: Optional[str],
+        call_trace_id: Optional[str],
+        call_properties: Optional[Dict[str, Any]],
+        call_privacy_mode: Optional[bool],
+        call_groups: Optional[Dict[str, Any]],
+    ):
+        """Merge call-level PostHog parameters with client defaults."""
+
+        # Use call-level values if provided, otherwise fall back to defaults
+        distinct_id = (
+            call_distinct_id
+            if call_distinct_id is not None
+            else self._default_distinct_id
+        )
+        privacy_mode = (
+            call_privacy_mode
+            if call_privacy_mode is not None
+            else self._default_privacy_mode
+        )
+        groups = call_groups if call_groups is not None else self._default_groups
+
+        # Merge properties: default properties + call properties (call properties override)
+        properties = dict(self._default_properties)
+
+        if call_properties:
+            properties.update(call_properties)
+
+        if call_trace_id is None:
+            call_trace_id = str(uuid.uuid4())
+
+        return distinct_id, call_trace_id, properties, privacy_mode, groups
+
+    async def generate_content(
+        self,
+        model: str,
+        contents,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: Optional[bool] = None,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        """
+        Generate content using Gemini's API while tracking usage in PostHog.
+
+        This method signature exactly matches genai.Client().aio.models.generate_content()
+        with additional PostHog tracking parameters.
+
+        Args:
+            model: The model to use (e.g., 'gemini-2.0-flash')
+            contents: The input content for generation
+            posthog_distinct_id: ID to associate with the usage event (overrides client default)
+            posthog_trace_id: Trace UUID for linking events (auto-generated if not provided)
+            posthog_properties: Extra properties to include in the event (merged with client defaults)
+            posthog_privacy_mode: Whether to redact sensitive information (overrides client default)
+            posthog_groups: Group analytics properties (overrides client default)
+            **kwargs: Arguments passed to Gemini's generate_content
+        """
+
+        # Merge PostHog parameters
+        distinct_id, trace_id, properties, privacy_mode, groups = (
+            self._merge_posthog_params(
+                posthog_distinct_id,
+                posthog_trace_id,
+                posthog_properties,
+                posthog_privacy_mode,
+                posthog_groups,
+            )
+        )
+
+        kwargs_with_contents = {"model": model, "contents": contents, **kwargs}
+
+        return await call_llm_and_track_usage_async(
+            distinct_id,
+            self._ph_client,
+            "gemini",
+            trace_id,
+            properties,
+            privacy_mode,
+            groups,
+            self._base_url,
+            self._client.aio.models.generate_content,
+            **kwargs_with_contents,
+        )
+
+    async def _generate_content_streaming(
+        self,
+        model: str,
+        contents,
+        distinct_id: Optional[str],
+        trace_id: Optional[str],
+        properties: Optional[Dict[str, Any]],
+        privacy_mode: bool,
+        groups: Optional[Dict[str, Any]],
+        **kwargs: Any,
+    ):
+        start_time = time.time()
+        usage_stats: TokenUsage = TokenUsage(input_tokens=0, output_tokens=0)
+        accumulated_content = []
+
+        kwargs_without_stream = {"model": model, "contents": contents, **kwargs}
+        response = await self._client.aio.models.generate_content_stream(
+            **kwargs_without_stream
+        )
+
+        async def async_generator():
+            nonlocal usage_stats
+            nonlocal accumulated_content
+
+            try:
+                async for chunk in response:
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_gemini_usage_from_chunk(chunk)
+
+                    if chunk_usage:
+                        # Gemini reports cumulative totals, not incremental values
+                        merge_usage_stats(usage_stats, chunk_usage, mode="cumulative")
+
+                    # Extract content from chunk (now returns content blocks)
+                    content_block = extract_gemini_content_from_chunk(chunk)
+
+                    if content_block is not None:
+                        accumulated_content.append(content_block)
+
+                    yield chunk
+
+            finally:
+                end_time = time.time()
+                latency = end_time - start_time
+
+                self._capture_streaming_event(
+                    model,
+                    contents,
+                    distinct_id,
+                    trace_id,
+                    properties,
+                    privacy_mode,
+                    groups,
+                    kwargs,
+                    usage_stats,
+                    latency,
+                    accumulated_content,
+                )
+
+        return async_generator()
+
+    def _capture_streaming_event(
+        self,
+        model: str,
+        contents,
+        distinct_id: Optional[str],
+        trace_id: Optional[str],
+        properties: Optional[Dict[str, Any]],
+        privacy_mode: bool,
+        groups: Optional[Dict[str, Any]],
+        kwargs: Dict[str, Any],
+        usage_stats: TokenUsage,
+        latency: float,
+        output: Any,
+    ):
+        # Prepare standardized event data
+        formatted_input = self._format_input(contents, **kwargs)
+        sanitized_input = sanitize_gemini(formatted_input)
+
+        event_data = StreamingEventData(
+            provider="gemini",
+            model=model,
+            base_url=self._base_url,
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_gemini_streaming_output(output),
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=distinct_id,
+            trace_id=trace_id,
+            properties=properties,
+            privacy_mode=privacy_mode,
+            groups=groups,
+        )
+
+        # Use the common capture function
+        capture_streaming_event(self._ph_client, event_data)
+
+    def _format_input(self, contents, **kwargs):
+        """Format input contents for PostHog tracking"""
+
+        # Create kwargs dict with contents for merge_system_prompt
+        input_kwargs = {"contents": contents, **kwargs}
+        return merge_system_prompt(input_kwargs, "gemini")
+
+    async def generate_content_stream(
+        self,
+        model: str,
+        contents,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: Optional[bool] = None,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        # Merge PostHog parameters
+        distinct_id, trace_id, properties, privacy_mode, groups = (
+            self._merge_posthog_params(
+                posthog_distinct_id,
+                posthog_trace_id,
+                posthog_properties,
+                posthog_privacy_mode,
+                posthog_groups,
+            )
+        )
+
+        return await self._generate_content_streaming(
+            model,
+            contents,
+            distinct_id,
+            trace_id,
+            properties,
+            privacy_mode,
+            groups,
+            **kwargs,
+        )

posthog/ai/gemini/gemini_converter.py

@@ -0,0 +1,652 @@
+"""
+Gemini-specific conversion utilities.
+
+This module handles the conversion of Gemini API responses and inputs
+into standardized formats for PostHog tracking.
+"""
+
+from typing import Any, Dict, List, Optional, TypedDict, Union
+
+from posthog.ai.types import (
+    FormattedContentItem,
+    FormattedMessage,
+    TokenUsage,
+)
+
+
+class GeminiPart(TypedDict, total=False):
+    """Represents a part in a Gemini message."""
+
+    text: str
+
+
+class GeminiMessage(TypedDict, total=False):
+    """Represents a Gemini message with various possible fields."""
+
+    role: str
+    parts: List[Union[GeminiPart, Dict[str, Any]]]
+    content: Union[str, List[Any]]
+    text: str
+
+
+def _format_parts_as_content_blocks(parts: List[Any]) -> List[FormattedContentItem]:
+    """
+    Format Gemini parts array into structured content blocks.
+
+    Preserves structure for multimodal content (text + images) instead of
+    concatenating everything into a string.
+
+    Args:
+        parts: List of parts that may contain text, inline_data, etc.
+
+    Returns:
+        List of formatted content blocks
+    """
+    content_blocks: List[FormattedContentItem] = []
+
+    for part in parts:
+        # Handle dict with text field
+        if isinstance(part, dict) and "text" in part:
+            content_blocks.append({"type": "text", "text": part["text"]})
+
+        # Handle string parts
+        elif isinstance(part, str):
+            content_blocks.append({"type": "text", "text": part})
+
+        # Handle dict with inline_data (images, documents, etc.)
+        elif isinstance(part, dict) and "inline_data" in part:
+            inline_data = part["inline_data"]
+            mime_type = inline_data.get("mime_type", "")
+            content_type = "image" if mime_type.startswith("image/") else "document"
+
+            content_blocks.append(
+                {
+                    "type": content_type,
+                    "inline_data": inline_data,
+                }
+            )
+
+        # Handle object with text attribute
+        elif hasattr(part, "text"):
+            text_value = getattr(part, "text", "")
+            if text_value:
+                content_blocks.append({"type": "text", "text": text_value})
+
+        # Handle object with inline_data attribute
+        elif hasattr(part, "inline_data"):
+            inline_data = part.inline_data
+            # Convert to dict if needed
+            if hasattr(inline_data, "mime_type") and hasattr(inline_data, "data"):
+                # Determine type based on mime_type
+                mime_type = inline_data.mime_type
+                content_type = "image" if mime_type.startswith("image/") else "document"
+
+                content_blocks.append(
+                    {
+                        "type": content_type,
+                        "inline_data": {
+                            "mime_type": mime_type,
+                            "data": inline_data.data,
+                        },
+                    }
+                )
+            else:
+                content_blocks.append(
+                    {
+                        "type": "image",
+                        "inline_data": inline_data,
+                    }
+                )
+
+    return content_blocks
+
+
+def _format_dict_message(item: Dict[str, Any]) -> FormattedMessage:
+    """
+    Format a dictionary message into standardized format.
+
+    Args:
+        item: Dictionary containing message data
+
+    Returns:
+        Formatted message with role and content
+    """
+
+    # Handle dict format with parts array (Gemini-specific format)
+    if "parts" in item and isinstance(item["parts"], list):
+        content_blocks = _format_parts_as_content_blocks(item["parts"])
+        return {"role": item.get("role", "user"), "content": content_blocks}
+
+    # Handle dict with content field
+    if "content" in item:
+        content = item["content"]
+
+        if isinstance(content, list):
+            # If content is a list, format it as content blocks
+            content_blocks = _format_parts_as_content_blocks(content)
+            return {"role": item.get("role", "user"), "content": content_blocks}
+
+        elif not isinstance(content, str):
+            content = str(content)
+
+        return {"role": item.get("role", "user"), "content": content}
+
+    # Handle dict with text field
+    if "text" in item:
+        return {"role": item.get("role", "user"), "content": item["text"]}
+
+    # Fallback to string representation
+    return {"role": "user", "content": str(item)}
+
+
+def _format_object_message(item: Any) -> FormattedMessage:
+    """
+    Format an object (with attributes) into standardized format.
+
+    Args:
+        item: Object that may have text or parts attributes
+
+    Returns:
+        Formatted message with role and content
+    """
+
+    # Handle object with parts attribute
+    if hasattr(item, "parts") and hasattr(item.parts, "__iter__"):
+        content_blocks = _format_parts_as_content_blocks(list(item.parts))
+        role = getattr(item, "role", "user") if hasattr(item, "role") else "user"
+
+        # Ensure role is a string
+        if not isinstance(role, str):
+            role = "user"
+
+        return {"role": role, "content": content_blocks}
+
+    # Handle object with text attribute
+    if hasattr(item, "text"):
+        role = getattr(item, "role", "user") if hasattr(item, "role") else "user"
+
+        # Ensure role is a string
+        if not isinstance(role, str):
+            role = "user"
+
+        return {"role": role, "content": item.text}
+
+    # Handle object with content attribute
+    if hasattr(item, "content"):
+        role = getattr(item, "role", "user") if hasattr(item, "role") else "user"
+
+        # Ensure role is a string
+        if not isinstance(role, str):
+            role = "user"
+
+        content = item.content
+
+        if isinstance(content, list):
+            content_blocks = _format_parts_as_content_blocks(content)
+            return {"role": role, "content": content_blocks}
+
+        elif not isinstance(content, str):
+            content = str(content)
+        return {"role": role, "content": content}
+
+    # Fallback to string representation
+    return {"role": "user", "content": str(item)}
+
+
+def format_gemini_response(response: Any) -> List[FormattedMessage]:
+    """
+    Format a Gemini response into standardized message format.
+
+    Args:
+        response: The response object from Gemini API
+
+    Returns:
+        List of formatted messages with role and content
+    """
+
+    output: List[FormattedMessage] = []
+
+    if response is None:
+        return output
+
+    if hasattr(response, "candidates") and response.candidates:
+        for candidate in response.candidates:
+            if hasattr(candidate, "content") and candidate.content:
+                content: List[FormattedContentItem] = []
+
+                if hasattr(candidate.content, "parts") and candidate.content.parts:
+                    for part in candidate.content.parts:
+                        if hasattr(part, "text") and part.text:
+                            content.append(
+                                {
+                                    "type": "text",
+                                    "text": part.text,
+                                }
+                            )
+
+                        elif hasattr(part, "function_call") and part.function_call:
+                            function_call = part.function_call
+                            content.append(
+                                {
+                                    "type": "function",
+                                    "function": {
+                                        "name": function_call.name,
+                                        "arguments": function_call.args,
+                                    },
+                                }
+                            )
+
+                        elif hasattr(part, "inline_data") and part.inline_data:
+                            # Handle audio/media inline data
+                            import base64
+
+                            inline_data = part.inline_data
+                            mime_type = getattr(inline_data, "mime_type", "audio/pcm")
+                            raw_data = getattr(inline_data, "data", b"")
+
+                            # Encode binary data as base64 string for JSON serialization
+                            if isinstance(raw_data, bytes):
+                                data = base64.b64encode(raw_data).decode("utf-8")
+                            else:
+                                # Already a string (base64)
+                                data = raw_data
+
+                            content.append(
+                                {
+                                    "type": "audio",
+                                    "mime_type": mime_type,
+                                    "data": data,
+                                }
+                            )
+
+                if content:
+                    output.append(
+                        {
+                            "role": "assistant",
+                            "content": content,
+                        }
+                    )
+
+            elif hasattr(candidate, "text") and candidate.text:
+                output.append(
+                    {
+                        "role": "assistant",
+                        "content": [{"type": "text", "text": candidate.text}],
+                    }
+                )
+
+    elif hasattr(response, "text") and response.text:
+        output.append(
+            {
+                "role": "assistant",
+                "content": [{"type": "text", "text": response.text}],
+            }
+        )
+
+    return output
+
+
+def extract_gemini_system_instruction(config: Any) -> Optional[str]:
+    """
+    Extract system instruction from Gemini config parameter.
+
+    Args:
+        config: Config object or dict that may contain system instruction
+
+    Returns:
+        System instruction string if present, None otherwise
+    """
+    if config is None:
+        return None
+
+    # Handle different config formats
+    if hasattr(config, "system_instruction"):
+        return config.system_instruction
+    elif isinstance(config, dict) and "system_instruction" in config:
+        return config["system_instruction"]
+    elif isinstance(config, dict) and "systemInstruction" in config:
+        return config["systemInstruction"]
+
+    return None
+
+
+def extract_gemini_tools(kwargs: Dict[str, Any]) -> Optional[Any]:
+    """
+    Extract tool definitions from Gemini API kwargs.
+
+    Args:
+        kwargs: Keyword arguments passed to Gemini API
+
+    Returns:
+        Tool definitions if present, None otherwise
+    """
+
+    if "config" in kwargs and hasattr(kwargs["config"], "tools"):
+        return kwargs["config"].tools
+
+    return None
+
+
+def format_gemini_input_with_system(
+    contents: Any, config: Any = None
+) -> List[FormattedMessage]:
+    """
+    Format Gemini input contents into standardized message format, including system instruction handling.
+
+    Args:
+        contents: Input contents in various possible formats
+        config: Config object or dict that may contain system instruction
+
+    Returns:
+        List of formatted messages with role and content fields, with system message prepended if needed
+    """
+    formatted_messages = format_gemini_input(contents)
+
+    # Check if system instruction is provided in config parameter
+    system_instruction = extract_gemini_system_instruction(config)
+
+    if system_instruction is not None:
+        has_system = any(msg.get("role") == "system" for msg in formatted_messages)
+        if not has_system:
+            from posthog.ai.types import FormattedMessage
+
+            system_message: FormattedMessage = {
+                "role": "system",
+                "content": system_instruction,
+            }
+            formatted_messages = [system_message] + list(formatted_messages)
+
+    return formatted_messages
+
+
+def format_gemini_input(contents: Any) -> List[FormattedMessage]:
+    """
+    Format Gemini input contents into standardized message format for PostHog tracking.
+
+    This function handles various input formats:
+    - String inputs
+    - List of strings, dicts, or objects
+    - Single dict or object
+    - Gemini-specific format with parts array
+
+    Args:
+        contents: Input contents in various possible formats
+
+    Returns:
+        List of formatted messages with role and content fields
+    """
+
+    # Handle string input
+    if isinstance(contents, str):
+        return [{"role": "user", "content": contents}]
+
+    # Handle list input
+    if isinstance(contents, list):
+        formatted: List[FormattedMessage] = []
+
+        for item in contents:
+            if isinstance(item, str):
+                formatted.append({"role": "user", "content": item})
+
+            elif isinstance(item, dict):
+                formatted.append(_format_dict_message(item))
+
+            else:
+                formatted.append(_format_object_message(item))
+
+        return formatted
+
+    # Handle single dict input
+    if isinstance(contents, dict):
+        return [_format_dict_message(contents)]
+
+    # Handle single object input
+    return [_format_object_message(contents)]
+
+
+def extract_gemini_web_search_count(response: Any) -> int:
+    """
+    Extract web search count from Gemini response.
+
+    Gemini bills per request that uses grounding, not per query.
+    Returns 1 if grounding_metadata is present with actual search data, 0 otherwise.
+
+    Args:
+        response: The response from Gemini API
+
+    Returns:
+        1 if web search/grounding was used, 0 otherwise
+    """
+
+    # Check for grounding_metadata in candidates
+    if hasattr(response, "candidates"):
+        for candidate in response.candidates:
+            if (
+                hasattr(candidate, "grounding_metadata")
+                and candidate.grounding_metadata
+            ):
+                grounding_metadata = candidate.grounding_metadata
+
+                # Check if web_search_queries exists and is non-empty
+                if hasattr(grounding_metadata, "web_search_queries"):
+                    queries = grounding_metadata.web_search_queries
+
+                    if queries is not None and len(queries) > 0:
+                        return 1
+
+                # Check if grounding_chunks exists and is non-empty
+                if hasattr(grounding_metadata, "grounding_chunks"):
+                    chunks = grounding_metadata.grounding_chunks
+
+                    if chunks is not None and len(chunks) > 0:
+                        return 1
+
+            # Also check for google_search or grounding in function call names
+            if hasattr(candidate, "content") and candidate.content:
+                if hasattr(candidate.content, "parts") and candidate.content.parts:
+                    for part in candidate.content.parts:
+                        if hasattr(part, "function_call") and part.function_call:
+                            function_name = getattr(
+                                part.function_call, "name", ""
+                            ).lower()
+
+                            if (
+                                "google_search" in function_name
+                                or "grounding" in function_name
+                            ):
+                                return 1
+
+    return 0
+
+
+def _extract_usage_from_metadata(metadata: Any) -> TokenUsage:
+    """
+    Common logic to extract usage from Gemini metadata.
+    Used by both streaming and non-streaming paths.
+
+    Args:
+        metadata: usage_metadata from Gemini response or chunk
+
+    Returns:
+        TokenUsage with standardized usage
+    """
+    usage = TokenUsage(
+        input_tokens=getattr(metadata, "prompt_token_count", 0),
+        output_tokens=getattr(metadata, "candidates_token_count", 0),
+    )
+
+    # Add cache tokens if present (don't add if 0)
+    if hasattr(metadata, "cached_content_token_count"):
+        cache_tokens = metadata.cached_content_token_count
+        if cache_tokens and cache_tokens > 0:
+            usage["cache_read_input_tokens"] = cache_tokens
+
+    # Add reasoning tokens if present (don't add if 0)
+    if hasattr(metadata, "thoughts_token_count"):
+        reasoning_tokens = metadata.thoughts_token_count
+        if reasoning_tokens and reasoning_tokens > 0:
+            usage["reasoning_tokens"] = reasoning_tokens
+
+    return usage
+
+
+def extract_gemini_usage_from_response(response: Any) -> TokenUsage:
+    """
+    Extract usage statistics from a full Gemini response (non-streaming).
+
+    Args:
+        response: The complete response from Gemini API
+
+    Returns:
+        TokenUsage with standardized usage statistics
+    """
+    if not hasattr(response, "usage_metadata") or not response.usage_metadata:
+        return TokenUsage(input_tokens=0, output_tokens=0)
+
+    usage = _extract_usage_from_metadata(response.usage_metadata)
+
+    # Add web search count if present
+    web_search_count = extract_gemini_web_search_count(response)
+    if web_search_count > 0:
+        usage["web_search_count"] = web_search_count
+
+    return usage
+
+
+def extract_gemini_usage_from_chunk(chunk: Any) -> TokenUsage:
+    """
+    Extract usage statistics from a Gemini streaming chunk.
+
+    Args:
+        chunk: Streaming chunk from Gemini API
+
+    Returns:
+        TokenUsage with standardized usage statistics
+    """
+
+    usage: TokenUsage = TokenUsage()
+
+    # Extract web search count from the chunk before checking for usage_metadata
+    # Web search indicators can appear on any chunk, not just those with usage data
+    web_search_count = extract_gemini_web_search_count(chunk)
+    if web_search_count > 0:
+        usage["web_search_count"] = web_search_count
+
+    if not hasattr(chunk, "usage_metadata") or not chunk.usage_metadata:
+        return usage
+
+    usage_from_metadata = _extract_usage_from_metadata(chunk.usage_metadata)
+
+    # Merge the usage from metadata with any web search count we found
+    usage.update(usage_from_metadata)
+
+    return usage
+
+
+def extract_gemini_content_from_chunk(chunk: Any) -> Optional[Dict[str, Any]]:
+    """
+    Extract content (text or function call) from a Gemini streaming chunk.
+
+    Args:
+        chunk: Streaming chunk from Gemini API
+
+    Returns:
+        Content block dictionary if present, None otherwise
+    """
+
+    # Check for text content
+    if hasattr(chunk, "text") and chunk.text:
+        return {"type": "text", "text": chunk.text}
+
+    # Check for function calls in candidates
+    if hasattr(chunk, "candidates") and chunk.candidates:
+        for candidate in chunk.candidates:
+            if hasattr(candidate, "content") and candidate.content:
+                if hasattr(candidate.content, "parts") and candidate.content.parts:
+                    for part in candidate.content.parts:
+                        # Check for function_call part
+                        if hasattr(part, "function_call") and part.function_call:
+                            function_call = part.function_call
+                            return {
+                                "type": "function",
+                                "function": {
+                                    "name": function_call.name,
+                                    "arguments": function_call.args,
+                                },
+                            }
+                        # Also check for text in parts
+                        elif hasattr(part, "text") and part.text:
+                            return {"type": "text", "text": part.text}
+
+    return None
+
+
+def format_gemini_streaming_output(
+    accumulated_content: Union[str, List[Any]],
+) -> List[FormattedMessage]:
+    """
+    Format the final output from Gemini streaming.
+
+    Args:
+        accumulated_content: Accumulated content from streaming (string, list of strings, or list of content blocks)
+
+    Returns:
+        List of formatted messages
+    """
+
+    # Handle legacy string input (backward compatibility)
+    if isinstance(accumulated_content, str):
+        return [
+            {
+                "role": "assistant",
+                "content": [{"type": "text", "text": accumulated_content}],
+            }
+        ]
+
+    # Handle list input
+    if isinstance(accumulated_content, list):
+        content: List[FormattedContentItem] = []
+        text_parts = []
+
+        for item in accumulated_content:
+            if isinstance(item, str):
+                # Legacy support: accumulate strings
+                text_parts.append(item)
+            elif isinstance(item, dict):
+                # New format: content blocks
+                if item.get("type") == "text":
+                    text_parts.append(item.get("text", ""))
+                elif item.get("type") == "function":
+                    # If we have accumulated text, add it first
+                    if text_parts:
+                        content.append(
+                            {
+                                "type": "text",
+                                "text": "".join(text_parts),
+                            }
+                        )
+                        text_parts = []
+
+                    # Add the function call
+                    content.append(
+                        {
+                            "type": "function",
+                            "function": item.get("function", {}),
+                        }
+                    )
+
+        # Add any remaining text
+        if text_parts:
+            content.append(
+                {
+                    "type": "text",
+                    "text": "".join(text_parts),
+                }
+            )
+
+        # If we have content, return it
+        if content:
+            return [{"role": "assistant", "content": content}]
+
+    # Fallback for empty or unexpected input
+    return [{"role": "assistant", "content": [{"type": "text", "text": ""}]}]

posthog/ai/langchain/callbacks.py

@@ -1,8 +1,11 @@
 try:
-    import langchain  # noqa: F401
+    import langchain_core  # noqa: F401
 except ImportError:
-    raise ModuleNotFoundError("Please install LangChain to use this feature: 'pip install langchain'")
+    raise ModuleNotFoundError(
+        "Please install LangChain to use this feature: 'pip install langchain-core'"
+    )
 
+import json
 import logging
 import time
 from dataclasses import dataclass
@@ -12,20 +15,34 @@ from typing import (
     List,
     Optional,
     Sequence,
-    Tuple,
     Union,
     cast,
 )
 from uuid import UUID
 
-from langchain.callbacks.base import BaseCallbackHandler
-from langchain.schema.agent import AgentAction, AgentFinish
+try:
+    # LangChain 1.0+ and modern 0.x with langchain-core
+    from langchain_core.agents import AgentAction, AgentFinish
+    from langchain_core.callbacks.base import BaseCallbackHandler
+except (ImportError, ModuleNotFoundError):
+    # Fallback for older LangChain versions
+    from langchain.callbacks.base import BaseCallbackHandler
+    from langchain.schema.agent import AgentAction, AgentFinish
 from langchain_core.documents import Document
-from langchain_core.messages import AIMessage, BaseMessage, FunctionMessage, HumanMessage, SystemMessage, ToolMessage
+from langchain_core.messages import (
+    AIMessage,
+    BaseMessage,
+    FunctionMessage,
+    HumanMessage,
+    SystemMessage,
+    ToolCall,
+    ToolMessage,
+)
 from langchain_core.outputs import ChatGeneration, LLMResult
 from pydantic import BaseModel
 
-from posthog import default_client
+from posthog import setup
+from posthog.ai.sanitization import sanitize_langchain
 from posthog.ai.utils import get_model_params, with_privacy_mode
 from posthog.client import Client
 
@@ -62,6 +79,8 @@ class GenerationMetadata(SpanMetadata):
     """Base URL of the provider's API used in the run."""
     tools: Optional[List[Dict[str, Any]]] = None
     """Tools provided to the model."""
+    posthog_properties: Optional[Dict[str, Any]] = None
+    """PostHog properties of the run."""
 
 
 RunMetadata = Union[SpanMetadata, GenerationMetadata]
@@ -73,10 +92,10 @@ class CallbackHandler(BaseCallbackHandler):
     The PostHog LLM observability callback handler for LangChain.
     """
 
-    _client: Client
+    _ph_client: Client
     """PostHog client instance."""
 
-    _distinct_id: Optional[Union[str, int, float, UUID]]
+    _distinct_id: Optional[Union[str, int, UUID]]
     """Distinct ID of the user to associate the trace with."""
 
     _trace_id: Optional[Union[str, int, float, UUID]]
@@ -104,7 +123,7 @@ class CallbackHandler(BaseCallbackHandler):
         self,
         client: Optional[Client] = None,
         *,
-        distinct_id: Optional[Union[str, int, float, UUID]] = None,
+        distinct_id: Optional[Union[str, int, UUID]] = None,
         trace_id: Optional[Union[str, int, float, UUID]] = None,
         properties: Optional[Dict[str, Any]] = None,
         privacy_mode: bool = False,
@@ -119,10 +138,7 @@ class CallbackHandler(BaseCallbackHandler):
             privacy_mode: Whether to redact the input and output of the trace.
             groups: Optional additional PostHog groups to use for the trace.
         """
-        posthog_client = client or default_client
-        if posthog_client is None:
-            raise ValueError("PostHog client is required")
-        self._client = posthog_client
+        self._ph_client = client or setup()
         self._distinct_id = distinct_id
         self._trace_id = trace_id
         self._properties = properties or {}
@@ -143,7 +159,9 @@ class CallbackHandler(BaseCallbackHandler):
     ):
         self._log_debug_event("on_chain_start", run_id, parent_run_id, inputs=inputs)
         self._set_parent_of_run(run_id, parent_run_id)
-        self._set_trace_or_span_metadata(serialized, inputs, run_id, parent_run_id, **kwargs)
+        self._set_trace_or_span_metadata(
+            serialized, inputs, run_id, parent_run_id, **kwargs
+        )
 
     def on_chain_end(
         self,
@@ -176,9 +194,13 @@ class CallbackHandler(BaseCallbackHandler):
         parent_run_id: Optional[UUID] = None,
         **kwargs,
     ):
-        self._log_debug_event("on_chat_model_start", run_id, parent_run_id, messages=messages)
+        self._log_debug_event(
+            "on_chat_model_start", run_id, parent_run_id, messages=messages
+        )
         self._set_parent_of_run(run_id, parent_run_id)
-        input = [_convert_message_to_dict(message) for row in messages for message in row]
+        input = [
+            _convert_message_to_dict(message) for row in messages for message in row
+        ]
         self._set_llm_metadata(serialized, run_id, input, **kwargs)
 
     def on_llm_start(
@@ -216,7 +238,9 @@ class CallbackHandler(BaseCallbackHandler):
         """
         The callback works for both streaming and non-streaming runs. For streaming runs, the chain must set `stream_usage=True` in the LLM.
         """
-        self._log_debug_event("on_llm_end", run_id, parent_run_id, response=response, kwargs=kwargs)
+        self._log_debug_event(
+            "on_llm_end", run_id, parent_run_id, response=response, kwargs=kwargs
+        )
         self._pop_run_and_capture_generation(run_id, parent_run_id, response)
 
     def on_llm_error(
@@ -240,9 +264,13 @@ class CallbackHandler(BaseCallbackHandler):
         metadata: Optional[Dict[str, Any]] = None,
         **kwargs: Any,
     ) -> Any:
-        self._log_debug_event("on_tool_start", run_id, parent_run_id, input_str=input_str)
+        self._log_debug_event(
+            "on_tool_start", run_id, parent_run_id, input_str=input_str
+        )
         self._set_parent_of_run(run_id, parent_run_id)
-        self._set_trace_or_span_metadata(serialized, input_str, run_id, parent_run_id, **kwargs)
+        self._set_trace_or_span_metadata(
+            serialized, input_str, run_id, parent_run_id, **kwargs
+        )
 
     def on_tool_end(
         self,
@@ -279,7 +307,9 @@ class CallbackHandler(BaseCallbackHandler):
     ) -> Any:
         self._log_debug_event("on_retriever_start", run_id, parent_run_id, query=query)
         self._set_parent_of_run(run_id, parent_run_id)
-        self._set_trace_or_span_metadata(serialized, query, run_id, parent_run_id, **kwargs)
+        self._set_trace_or_span_metadata(
+            serialized, query, run_id, parent_run_id, **kwargs
+        )
 
     def on_retriever_end(
         self,
@@ -289,7 +319,9 @@ class CallbackHandler(BaseCallbackHandler):
         parent_run_id: Optional[UUID] = None,
         **kwargs: Any,
     ):
-        self._log_debug_event("on_retriever_end", run_id, parent_run_id, documents=documents)
+        self._log_debug_event(
+            "on_retriever_end", run_id, parent_run_id, documents=documents
+        )
         self._pop_run_and_capture_trace_or_span(run_id, parent_run_id, documents)
 
     def on_retriever_error(
@@ -364,7 +396,9 @@ class CallbackHandler(BaseCallbackHandler):
     ):
         default_name = "trace" if parent_run_id is None else "span"
         run_name = _get_langchain_run_name(serialized, **kwargs) or default_name
-        self._runs[run_id] = SpanMetadata(name=run_name, input=input, start_time=time.time(), end_time=None)
+        self._runs[run_id] = SpanMetadata(
+            name=run_name, input=input, start_time=time.time(), end_time=None
+        )
 
     def _set_llm_metadata(
         self,
@@ -376,7 +410,9 @@ class CallbackHandler(BaseCallbackHandler):
         **kwargs,
     ):
         run_name = _get_langchain_run_name(serialized, **kwargs) or "generation"
-        generation = GenerationMetadata(name=run_name, input=messages, start_time=time.time(), end_time=None)
+        generation = GenerationMetadata(
+            name=run_name, input=messages, start_time=time.time(), end_time=None
+        )
         if isinstance(invocation_params, dict):
             generation.model_params = get_model_params(invocation_params)
             if tools := invocation_params.get("tools"):
@@ -386,6 +422,8 @@ class CallbackHandler(BaseCallbackHandler):
                 generation.model = model
             if provider := metadata.get("ls_provider"):
                 generation.provider = provider
+
+            generation.posthog_properties = metadata.get("posthog_properties")
         try:
             base_url = serialized["kwargs"]["openai_api_base"]
             if base_url is not None:
@@ -410,7 +448,9 @@ class CallbackHandler(BaseCallbackHandler):
             return run_id
         return trace_id
 
-    def _get_parent_run_id(self, trace_id: Any, run_id: UUID, parent_run_id: Optional[UUID]):
+    def _get_parent_run_id(
+        self, trace_id: Any, run_id: UUID, parent_run_id: Optional[UUID]
+    ):
         """
         Replace the parent run ID with the trace ID for second level runs when a custom trace ID is set.
         """
@@ -418,14 +458,18 @@ class CallbackHandler(BaseCallbackHandler):
             return trace_id
         return parent_run_id
 
-    def _pop_run_and_capture_trace_or_span(self, run_id: UUID, parent_run_id: Optional[UUID], outputs: Any):
+    def _pop_run_and_capture_trace_or_span(
+        self, run_id: UUID, parent_run_id: Optional[UUID], outputs: Any
+    ):
         trace_id = self._get_trace_id(run_id)
         self._pop_parent_of_run(run_id)
         run = self._pop_run_metadata(run_id)
         if not run:
             return
         if isinstance(run, GenerationMetadata):
-            log.warning(f"Run {run_id} is a generation, but attempted to be captured as a trace or span.")
+            log.warning(
+                f"Run {run_id} is a generation, but attempted to be captured as a trace or span."
+            )
             return
         self._capture_trace_or_span(
             trace_id,
@@ -446,10 +490,13 @@ class CallbackHandler(BaseCallbackHandler):
         event_name = "$ai_trace" if parent_run_id is None else "$ai_span"
         event_properties = {
             "$ai_trace_id": trace_id,
-            "$ai_input_state": with_privacy_mode(self._client, self._privacy_mode, run.input),
+            "$ai_input_state": with_privacy_mode(
+                self._ph_client, self._privacy_mode, sanitize_langchain(run.input)
+            ),
             "$ai_latency": run.latency,
             "$ai_span_name": run.name,
             "$ai_span_id": run_id,
+            "$ai_framework": "langchain",
         }
         if parent_run_id is not None:
             event_properties["$ai_parent_id"] = parent_run_id
@@ -459,13 +506,23 @@ class CallbackHandler(BaseCallbackHandler):
         if isinstance(outputs, BaseException):
             event_properties["$ai_error"] = _stringify_exception(outputs)
             event_properties["$ai_is_error"] = True
+            event_properties = _capture_exception_and_update_properties(
+                self._ph_client,
+                outputs,
+                self._distinct_id,
+                self._groups,
+                event_properties,
+            )
+
         elif outputs is not None:
-            event_properties["$ai_output_state"] = with_privacy_mode(self._client, self._privacy_mode, outputs)
+            event_properties["$ai_output_state"] = with_privacy_mode(
+                self._ph_client, self._privacy_mode, outputs
+            )
 
         if self._distinct_id is None:
             event_properties["$process_person_profile"] = False
 
-        self._client.capture(
+        self._ph_client.capture(
             distinct_id=self._distinct_id or run_id,
             event=event_name,
             properties=event_properties,
@@ -484,7 +541,9 @@ class CallbackHandler(BaseCallbackHandler):
         if not run:
             return
         if not isinstance(run, GenerationMetadata):
-            log.warning(f"Run {run_id} is not a generation, but attempted to be captured as a generation.")
+            log.warning(
+                f"Run {run_id} is not a generation, but attempted to be captured as a generation."
+            )
             return
         self._capture_generation(
             trace_id,
@@ -510,27 +569,49 @@ class CallbackHandler(BaseCallbackHandler):
             "$ai_provider": run.provider,
             "$ai_model": run.model,
             "$ai_model_parameters": run.model_params,
-            "$ai_input": with_privacy_mode(self._client, self._privacy_mode, run.input),
+            "$ai_input": with_privacy_mode(
+                self._ph_client, self._privacy_mode, sanitize_langchain(run.input)
+            ),
             "$ai_http_status": 200,
             "$ai_latency": run.latency,
             "$ai_base_url": run.base_url,
+            "$ai_framework": "langchain",
         }
+
+        if isinstance(run.posthog_properties, dict):
+            event_properties.update(run.posthog_properties)
+
         if run.tools:
-            event_properties["$ai_tools"] = with_privacy_mode(
-                self._client,
-                self._privacy_mode,
-                run.tools,
-            )
+            event_properties["$ai_tools"] = run.tools
+
+        if self._properties:
+            event_properties.update(self._properties)
+
+        if self._distinct_id is None:
+            event_properties["$process_person_profile"] = False
 
         if isinstance(output, BaseException):
             event_properties["$ai_http_status"] = _get_http_status(output)
             event_properties["$ai_error"] = _stringify_exception(output)
             event_properties["$ai_is_error"] = True
+
+            event_properties = _capture_exception_and_update_properties(
+                self._ph_client,
+                output,
+                self._distinct_id,
+                self._groups,
+                event_properties,
+            )
         else:
             # Add usage
-            input_tokens, output_tokens = _parse_usage(output)
-            event_properties["$ai_input_tokens"] = input_tokens
-            event_properties["$ai_output_tokens"] = output_tokens
+            usage = _parse_usage(output, run.provider, run.model)
+            event_properties["$ai_input_tokens"] = usage.input_tokens
+            event_properties["$ai_output_tokens"] = usage.output_tokens
+            event_properties["$ai_cache_creation_input_tokens"] = (
+                usage.cache_write_tokens
+            )
+            event_properties["$ai_cache_read_input_tokens"] = usage.cache_read_tokens
+            event_properties["$ai_reasoning_tokens"] = usage.reasoning_tokens
 
             # Generation results
             generation_result = output.generations[-1]
@@ -540,16 +621,15 @@ class CallbackHandler(BaseCallbackHandler):
                     for generation in generation_result
                 ]
             else:
-                completions = [_extract_raw_esponse(generation) for generation in generation_result]
-            event_properties["$ai_output_choices"] = with_privacy_mode(self._client, self._privacy_mode, completions)
+                completions = [
+                    _extract_raw_response(generation)
+                    for generation in generation_result
+                ]
+            event_properties["$ai_output_choices"] = with_privacy_mode(
+                self._ph_client, self._privacy_mode, completions
+            )
 
-        if self._properties:
-            event_properties.update(self._properties)
-
-        if self._distinct_id is None:
-            event_properties["$process_person_profile"] = False
-
-        self._client.capture(
+        self._ph_client.capture(
             distinct_id=self._distinct_id or trace_id,
             event="$ai_generation",
             properties=event_properties,
@@ -568,7 +648,7 @@ class CallbackHandler(BaseCallbackHandler):
         )
 
 
-def _extract_raw_esponse(last_response):
+def _extract_raw_response(last_response):
     """Extract the response from the last response of the LLM call."""
     # We return the text of the response if not empty
     if last_response.text is not None and last_response.text.strip() != "":
@@ -581,12 +661,35 @@ def _extract_raw_esponse(last_response):
         return ""
 
 
-def _convert_message_to_dict(message: BaseMessage) -> Dict[str, Any]:
+def _convert_lc_tool_calls_to_oai(
+    tool_calls: list[ToolCall],
+) -> list[dict[str, Any]]:
+    try:
+        return [
+            {
+                "type": "function",
+                "id": tool_call["id"],
+                "function": {
+                    "name": tool_call["name"],
+                    "arguments": json.dumps(tool_call["args"]),
+                },
+            }
+            for tool_call in tool_calls
+        ]
+    except KeyError:
+        return tool_calls
+
+
+def _convert_message_to_dict(message: BaseMessage) -> dict[str, Any]:
     # assistant message
     if isinstance(message, HumanMessage):
         message_dict = {"role": "user", "content": message.content}
     elif isinstance(message, AIMessage):
         message_dict = {"role": "assistant", "content": message.content}
+        if message.tool_calls:
+            message_dict["tool_calls"] = _convert_lc_tool_calls_to_oai(
+                message.tool_calls
+            )
     elif isinstance(message, SystemMessage):
         message_dict = {"role": "system", "content": message.content}
     elif isinstance(message, ToolMessage):
@@ -599,12 +702,26 @@ def _convert_message_to_dict(message: BaseMessage) -> Dict[str, Any]:
     if message.additional_kwargs:
         message_dict.update(message.additional_kwargs)
 
+    if "content" in message_dict and not message_dict["content"]:
+        message_dict["content"] = ""
+
     return message_dict
 
 
+@dataclass
+class ModelUsage:
+    input_tokens: Optional[int]
+    output_tokens: Optional[int]
+    cache_write_tokens: Optional[int]
+    cache_read_tokens: Optional[int]
+    reasoning_tokens: Optional[int]
+
+
 def _parse_usage_model(
-    usage: Union[BaseModel, Dict],
-) -> Tuple[Union[int, None], Union[int, None]]:
+    usage: Union[BaseModel, dict],
+    provider: Optional[str] = None,
+    model: Optional[str] = None,
+) -> ModelUsage:
     if isinstance(usage, BaseModel):
         usage = usage.__dict__
 
@@ -612,15 +729,23 @@ def _parse_usage_model(
         # https://pypi.org/project/langchain-anthropic/ (works also for Bedrock-Anthropic)
         ("input_tokens", "input"),
         ("output_tokens", "output"),
+        ("cache_creation_input_tokens", "cache_write"),
+        ("cache_read_input_tokens", "cache_read"),
         # https://cloud.google.com/vertex-ai/generative-ai/docs/multimodal/get-token-count
         ("prompt_token_count", "input"),
         ("candidates_token_count", "output"),
+        ("cached_content_token_count", "cache_read"),
+        ("thoughts_token_count", "reasoning"),
         # Bedrock: https://docs.aws.amazon.com/bedrock/latest/userguide/monitoring-cw.html#runtime-cloudwatch-metrics
         ("inputTokenCount", "input"),
         ("outputTokenCount", "output"),
+        ("cacheCreationInputTokenCount", "cache_write"),
+        ("cacheReadInputTokenCount", "cache_read"),
         # Bedrock Anthropic
         ("prompt_tokens", "input"),
         ("completion_tokens", "output"),
+        ("cache_creation_input_tokens", "cache_write"),
+        ("cache_read_input_tokens", "cache_read"),
         # langchain-ibm https://pypi.org/project/langchain-ibm/
         ("input_token_count", "input"),
         ("generated_token_count", "output"),
@@ -631,33 +756,98 @@ def _parse_usage_model(
         if model_key in usage:
             captured_count = usage[model_key]
             final_count = (
-                sum(captured_count) if isinstance(captured_count, list) else captured_count
+                sum(captured_count)
+                if isinstance(captured_count, list)
+                else captured_count
             )  # For Bedrock, the token count is a list when streamed
 
             parsed_usage[type_key] = final_count
 
-    return parsed_usage.get("input"), parsed_usage.get("output")
+    # Caching (OpenAI & langchain 0.3.9+)
+    if "input_token_details" in usage and isinstance(
+        usage["input_token_details"], dict
+    ):
+        parsed_usage["cache_write"] = usage["input_token_details"].get("cache_creation")
+        parsed_usage["cache_read"] = usage["input_token_details"].get("cache_read")
+
+    # Reasoning (OpenAI & langchain 0.3.9+)
+    if "output_token_details" in usage and isinstance(
+        usage["output_token_details"], dict
+    ):
+        parsed_usage["reasoning"] = usage["output_token_details"].get("reasoning")
+
+    field_mapping = {
+        "input": "input_tokens",
+        "output": "output_tokens",
+        "cache_write": "cache_write_tokens",
+        "cache_read": "cache_read_tokens",
+        "reasoning": "reasoning_tokens",
+    }
+    normalized_usage = ModelUsage(
+        **{
+            dataclass_key: parsed_usage.get(mapped_key) or 0
+            for mapped_key, dataclass_key in field_mapping.items()
+        },
+    )
+    # For Anthropic providers, LangChain reports input_tokens as the sum of all input tokens.
+    # Our cost calculation expects them to be separate for Anthropic, so we subtract cache tokens.
+    # Both cache_read and cache_write tokens should be subtracted since Anthropic's raw API
+    # reports input_tokens as tokens NOT read from or used to create a cache.
+    # For other providers (OpenAI, etc.), input_tokens already excludes cache tokens as expected.
+    # Match logic consistent with plugin-server: exact match on provider OR substring match on model
+    is_anthropic = False
+    if provider and provider.lower() == "anthropic":
+        is_anthropic = True
+    elif model and "anthropic" in model.lower():
+        is_anthropic = True
+
+    if is_anthropic and normalized_usage.input_tokens:
+        cache_tokens = (normalized_usage.cache_read_tokens or 0) + (
+            normalized_usage.cache_write_tokens or 0
+        )
+        if cache_tokens > 0:
+            normalized_usage.input_tokens = max(
+                normalized_usage.input_tokens - cache_tokens, 0
+            )
+    return normalized_usage
 
 
-def _parse_usage(response: LLMResult):
+def _parse_usage(
+    response: LLMResult, provider: Optional[str] = None, model: Optional[str] = None
+) -> ModelUsage:
     # langchain-anthropic uses the usage field
     llm_usage_keys = ["token_usage", "usage"]
-    llm_usage: Tuple[Union[int, None], Union[int, None]] = (None, None)
+    llm_usage: ModelUsage = ModelUsage(
+        input_tokens=None,
+        output_tokens=None,
+        cache_write_tokens=None,
+        cache_read_tokens=None,
+        reasoning_tokens=None,
+    )
+
     if response.llm_output is not None:
         for key in llm_usage_keys:
             if response.llm_output.get(key):
-                llm_usage = _parse_usage_model(response.llm_output[key])
+                llm_usage = _parse_usage_model(
+                    response.llm_output[key], provider, model
+                )
                 break
 
     if hasattr(response, "generations"):
         for generation in response.generations:
             if "usage" in generation:
-                llm_usage = _parse_usage_model(generation["usage"])
+                llm_usage = _parse_usage_model(generation["usage"], provider, model)
                 break
 
             for generation_chunk in generation:
-                if generation_chunk.generation_info and ("usage_metadata" in generation_chunk.generation_info):
-                    llm_usage = _parse_usage_model(generation_chunk.generation_info["usage_metadata"])
+                if generation_chunk.generation_info and (
+                    "usage_metadata" in generation_chunk.generation_info
+                ):
+                    llm_usage = _parse_usage_model(
+                        generation_chunk.generation_info["usage_metadata"],
+                        provider,
+                        model,
+                    )
                     break
 
                 message_chunk = getattr(generation_chunk, "message", {})
@@ -669,20 +859,47 @@ def _parse_usage(response: LLMResult):
                     else None
                 )
                 bedrock_titan_usage = (
-                    response_metadata.get("amazon-bedrock-invocationMetrics", None)  # for Bedrock-Titan
+                    response_metadata.get(
+                        "amazon-bedrock-invocationMetrics", None
+                    )  # for Bedrock-Titan
                     if isinstance(response_metadata, dict)
                     else None
                 )
-                ollama_usage = getattr(message_chunk, "usage_metadata", None)  # for Ollama
+                ollama_usage = getattr(
+                    message_chunk, "usage_metadata", None
+                )  # for Ollama
 
-                chunk_usage = bedrock_anthropic_usage or bedrock_titan_usage or ollama_usage
+                chunk_usage = (
+                    bedrock_anthropic_usage or bedrock_titan_usage or ollama_usage
+                )
                 if chunk_usage:
-                    llm_usage = _parse_usage_model(chunk_usage)
+                    llm_usage = _parse_usage_model(chunk_usage, provider, model)
                     break
 
     return llm_usage
 
 
+def _capture_exception_and_update_properties(
+    client: Client,
+    exception: BaseException,
+    distinct_id: Optional[Union[str, int, UUID]],
+    groups: Optional[Dict[str, Any]],
+    event_properties: Dict[str, Any],
+):
+    if client.enable_exception_autocapture:
+        exception_id = client.capture_exception(
+            exception,
+            distinct_id=distinct_id,
+            groups=groups,
+            properties=event_properties,
+        )
+
+        if exception_id:
+            event_properties["$exception_event_id"] = exception_id
+
+    return event_properties
+
+
 def _get_http_status(error: BaseException) -> int:
     # OpenAI: https://github.com/openai/openai-python/blob/main/src/openai/_exceptions.py
     # Anthropic: https://github.com/anthropics/anthropic-sdk-python/blob/main/src/anthropic/_exceptions.py
@@ -691,7 +908,9 @@ def _get_http_status(error: BaseException) -> int:
     return status_code
 
 
-def _get_langchain_run_name(serialized: Optional[Dict[str, Any]], **kwargs: Any) -> Optional[str]:
+def _get_langchain_run_name(
+    serialized: Optional[Dict[str, Any]], **kwargs: Any
+) -> Optional[str]:
     """Retrieve the name of a serialized LangChain runnable.
 
     The prioritization for the determination of the run name is as follows:

posthog/ai/openai/__init__.py

@@ -1,5 +1,20 @@
 from .openai import OpenAI
 from .openai_async import AsyncOpenAI
 from .openai_providers import AsyncAzureOpenAI, AzureOpenAI
+from .openai_converter import (
+    format_openai_response,
+    format_openai_input,
+    extract_openai_tools,
+    format_openai_streaming_content,
+)
 
-__all__ = ["OpenAI", "AsyncOpenAI", "AzureOpenAI", "AsyncAzureOpenAI"]
+__all__ = [
+    "OpenAI",
+    "AsyncOpenAI",
+    "AzureOpenAI",
+    "AsyncAzureOpenAI",
+    "format_openai_response",
+    "format_openai_input",
+    "extract_openai_tools",
+    "format_openai_streaming_content",
+]

posthog/ai/openai/openai.py

@@ -2,14 +2,30 @@ import time
 import uuid
 from typing import Any, Dict, List, Optional
 
+from posthog.ai.types import TokenUsage
+
 try:
     import openai
-    import openai.resources
 except ImportError:
-    raise ModuleNotFoundError("Please install the OpenAI SDK to use this feature: 'pip install openai'")
+    raise ModuleNotFoundError(
+        "Please install the OpenAI SDK to use this feature: 'pip install openai'"
+    )
 
-from posthog.ai.utils import call_llm_and_track_usage, get_model_params, with_privacy_mode
+from posthog.ai.utils import (
+    call_llm_and_track_usage,
+    extract_available_tool_calls,
+    merge_usage_stats,
+    with_privacy_mode,
+)
+from posthog.ai.openai.openai_converter import (
+    extract_openai_usage_from_chunk,
+    extract_openai_content_from_chunk,
+    extract_openai_tool_calls_from_chunk,
+    accumulate_openai_tool_calls,
+)
+from posthog.ai.sanitization import sanitize_openai, sanitize_openai_response
 from posthog.client import Client as PostHogClient
+from posthog import setup
 
 
 class OpenAI(openai.OpenAI):
@@ -19,24 +35,47 @@ class OpenAI(openai.OpenAI):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         """
         Args:
             api_key: OpenAI API key.
-            posthog_client: If provided, events will be captured via this client instead
-                            of the global posthog.
+            posthog_client: If provided, events will be captured via this client instead of the global `posthog`.
             **openai_config: Any additional keyword args to set on openai (e.g. organization="xxx").
         """
+
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
-        self.chat = WrappedChat(self)
-        self.embeddings = WrappedEmbeddings(self)
-        self.beta = WrappedBeta(self)
-        self.responses = WrappedResponses(self)
+        self._ph_client = posthog_client or setup()
+
+        # Store original objects after parent initialization (only if they exist)
+        self._original_chat = getattr(self, "chat", None)
+        self._original_embeddings = getattr(self, "embeddings", None)
+        self._original_beta = getattr(self, "beta", None)
+        self._original_responses = getattr(self, "responses", None)
+
+        # Replace with wrapped versions (only if originals exist)
+        if self._original_chat is not None:
+            self.chat = WrappedChat(self, self._original_chat)
+
+        if self._original_embeddings is not None:
+            self.embeddings = WrappedEmbeddings(self, self._original_embeddings)
+
+        if self._original_beta is not None:
+            self.beta = WrappedBeta(self, self._original_beta)
+
+        if self._original_responses is not None:
+            self.responses = WrappedResponses(self, self._original_responses)
 
 
-class WrappedResponses(openai.resources.responses.Responses):
-    _client: OpenAI
+class WrappedResponses:
+    """Wrapper for OpenAI responses that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_responses):
+        self._client = client
+        self._original = original_responses
+
+    def __getattr__(self, name):
+        """Fallback to original responses object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     def create(
         self,
@@ -69,7 +108,7 @@ class WrappedResponses(openai.resources.responses.Responses):
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().create,
+            self._original.create,
             **kwargs,
         )
 
@@ -83,41 +122,36 @@ class WrappedResponses(openai.resources.responses.Responses):
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {}
+        usage_stats: TokenUsage = TokenUsage()
         final_content = []
-        response = super().create(**kwargs)
+        model_from_response: Optional[str] = None
+        response = self._original.create(**kwargs)
 
         def generator():
             nonlocal usage_stats
             nonlocal final_content  # noqa: F824
+            nonlocal model_from_response
 
             try:
                 for chunk in response:
-                    if hasattr(chunk, "type") and chunk.type == "response.completed":
-                        res = chunk.response
-                        if res.output and len(res.output) > 0:
-                            final_content.append(res.output[0])
-
-                    if hasattr(chunk, "usage") and chunk.usage:
-                        usage_stats = {
-                            k: getattr(chunk.usage, k, 0)
-                            for k in [
-                                "input_tokens",
-                                "output_tokens",
-                                "total_tokens",
-                            ]
-                        }
-
-                        # Add support for cached tokens
-                        if hasattr(chunk.usage, "output_tokens_details") and hasattr(
-                            chunk.usage.output_tokens_details, "reasoning_tokens"
+                    # Extract model from response object in chunk (for stored prompts)
+                    if hasattr(chunk, "response") and chunk.response:
+                        if model_from_response is None and hasattr(
+                            chunk.response, "model"
                         ):
-                            usage_stats["reasoning_tokens"] = chunk.usage.output_tokens_details.reasoning_tokens
+                            model_from_response = chunk.response.model
 
-                        if hasattr(chunk.usage, "input_tokens_details") and hasattr(
-                            chunk.usage.input_tokens_details, "cached_tokens"
-                        ):
-                            usage_stats["cache_read_input_tokens"] = chunk.usage.input_tokens_details.cached_tokens
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_openai_usage_from_chunk(chunk, "responses")
+
+                    if chunk_usage:
+                        merge_usage_stats(usage_stats, chunk_usage)
+
+                    # Extract content from chunk
+                    content = extract_openai_content_from_chunk(chunk, "responses")
+
+                    if content is not None:
+                        final_content.append(content)
 
                     yield chunk
 
@@ -135,6 +169,8 @@ class WrappedResponses(openai.resources.responses.Responses):
                     usage_stats,
                     latency,
                     output,
+                    None,  # Responses API doesn't have tools
+                    model_from_response,
                 )
 
         return generator()
@@ -147,64 +183,108 @@ class WrappedResponses(openai.resources.responses.Responses):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
         output: Any,
-        tool_calls: Optional[List[Dict[str, Any]]] = None,
+        available_tool_calls: Optional[List[Dict[str, Any]]] = None,
+        model_from_response: Optional[str] = None,
     ):
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        from posthog.ai.types import StreamingEventData
+        from posthog.ai.openai.openai_converter import (
+            format_openai_streaming_input,
+            format_openai_streaming_output,
+        )
+        from posthog.ai.utils import capture_streaming_event
 
-        event_properties = {
-            "$ai_provider": "openai",
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("input")),
-            "$ai_output_choices": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                output,
-            ),
-            "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("input_tokens", 0),
-            "$ai_output_tokens": usage_stats.get("output_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
-            "$ai_reasoning_tokens": usage_stats.get("reasoning_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(self._client.base_url),
-            **(posthog_properties or {}),
-        }
+        # Prepare standardized event data
+        formatted_input = format_openai_streaming_input(kwargs, "responses")
+        sanitized_input = sanitize_openai_response(formatted_input)
 
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                tool_calls,
-            )
+        # Use model from kwargs, fallback to model from response
+        model = kwargs.get("model") or model_from_response or "unknown"
 
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
+        event_data = StreamingEventData(
+            provider="openai",
+            model=model,
+            base_url=str(self._client.base_url),
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_openai_streaming_output(output, "responses"),
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=posthog_distinct_id,
+            trace_id=posthog_trace_id,
+            properties=posthog_properties,
+            privacy_mode=posthog_privacy_mode,
+            groups=posthog_groups,
+        )
 
-        if hasattr(self._client._ph_client, "capture"):
-            self._client._ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
-            )
+        # Use the common capture function
+        capture_streaming_event(self._client._ph_client, event_data)
+
+    def parse(
+        self,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        """
+        Parse structured output using OpenAI's 'responses.parse' method, but also track usage in PostHog.
+
+        Args:
+            posthog_distinct_id: Optional ID to associate with the usage event.
+            posthog_trace_id: Optional trace UUID for linking events.
+            posthog_properties: Optional dictionary of extra properties to include in the event.
+            posthog_privacy_mode: Whether to anonymize the input and output.
+            posthog_groups: Optional dictionary of groups to associate with the event.
+            **kwargs: Any additional parameters for the OpenAI Responses Parse API.
+
+        Returns:
+            The response from OpenAI's responses.parse call.
+        """
+        return call_llm_and_track_usage(
+            posthog_distinct_id,
+            self._client._ph_client,
+            "openai",
+            posthog_trace_id,
+            posthog_properties,
+            posthog_privacy_mode,
+            posthog_groups,
+            self._client.base_url,
+            self._original.parse,
+            **kwargs,
+        )
 
 
-class WrappedChat(openai.resources.chat.Chat):
-    _client: OpenAI
+class WrappedChat:
+    """Wrapper for OpenAI chat that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_chat):
+        self._client = client
+        self._original = original_chat
+
+    def __getattr__(self, name):
+        """Fallback to original chat object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     @property
     def completions(self):
-        return WrappedCompletions(self._client)
+        return WrappedCompletions(self._client, self._original.completions)
 
 
-class WrappedCompletions(openai.resources.chat.completions.Completions):
-    _client: OpenAI
+class WrappedCompletions:
+    """Wrapper for OpenAI chat completions that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_completions):
+        self._client = client
+        self._original = original_completions
+
+    def __getattr__(self, name):
+        """Fallback to original completions object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     def create(
         self,
@@ -237,7 +317,7 @@ class WrappedCompletions(openai.resources.chat.completions.Completions):
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().create,
+            self._original.create,
             **kwargs,
         )
 
@@ -251,67 +331,59 @@ class WrappedCompletions(openai.resources.chat.completions.Completions):
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {}
+        usage_stats: TokenUsage = TokenUsage()
         accumulated_content = []
-        accumulated_tools = {}
+        accumulated_tool_calls: Dict[int, Dict[str, Any]] = {}
+        model_from_response: Optional[str] = None
         if "stream_options" not in kwargs:
             kwargs["stream_options"] = {}
         kwargs["stream_options"]["include_usage"] = True
-        response = super().create(**kwargs)
+        response = self._original.create(**kwargs)
 
         def generator():
             nonlocal usage_stats
             nonlocal accumulated_content  # noqa: F824
-            nonlocal accumulated_tools  # noqa: F824
+            nonlocal accumulated_tool_calls
+            nonlocal model_from_response
 
             try:
                 for chunk in response:
-                    if hasattr(chunk, "usage") and chunk.usage:
-                        usage_stats = {
-                            k: getattr(chunk.usage, k, 0)
-                            for k in [
-                                "prompt_tokens",
-                                "completion_tokens",
-                                "total_tokens",
-                            ]
-                        }
+                    # Extract model from chunk (Chat Completions chunks have model field)
+                    if model_from_response is None and hasattr(chunk, "model"):
+                        model_from_response = chunk.model
 
-                        # Add support for cached tokens
-                        if hasattr(chunk.usage, "prompt_tokens_details") and hasattr(
-                            chunk.usage.prompt_tokens_details, "cached_tokens"
-                        ):
-                            usage_stats["cache_read_input_tokens"] = chunk.usage.prompt_tokens_details.cached_tokens
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_openai_usage_from_chunk(chunk, "chat")
 
-                        if hasattr(chunk.usage, "output_tokens_details") and hasattr(
-                            chunk.usage.output_tokens_details, "reasoning_tokens"
-                        ):
-                            usage_stats["reasoning_tokens"] = chunk.usage.output_tokens_details.reasoning_tokens
+                    if chunk_usage:
+                        merge_usage_stats(usage_stats, chunk_usage)
 
-                    if hasattr(chunk, "choices") and chunk.choices and len(chunk.choices) > 0:
-                        if chunk.choices[0].delta and chunk.choices[0].delta.content:
-                            content = chunk.choices[0].delta.content
-                            if content:
-                                accumulated_content.append(content)
+                    # Extract content from chunk
+                    content = extract_openai_content_from_chunk(chunk, "chat")
 
-                        # Process tool calls
-                        tool_calls = getattr(chunk.choices[0].delta, "tool_calls", None)
-                        if tool_calls:
-                            for tool_call in tool_calls:
-                                index = tool_call.index
-                                if index not in accumulated_tools:
-                                    accumulated_tools[index] = tool_call
-                                else:
-                                    # Append arguments for existing tool calls
-                                    if hasattr(tool_call, "function") and hasattr(tool_call.function, "arguments"):
-                                        accumulated_tools[index].function.arguments += tool_call.function.arguments
+                    if content is not None:
+                        accumulated_content.append(content)
+
+                    # Extract and accumulate tool calls from chunk
+                    chunk_tool_calls = extract_openai_tool_calls_from_chunk(chunk)
+                    if chunk_tool_calls:
+                        accumulate_openai_tool_calls(
+                            accumulated_tool_calls, chunk_tool_calls
+                        )
 
                     yield chunk
 
             finally:
                 end_time = time.time()
                 latency = end_time - start_time
-                output = "".join(accumulated_content)
-                tools = list(accumulated_tools.values()) if accumulated_tools else None
+
+                # Convert accumulated tool calls dict to list
+                tool_calls_list = (
+                    list(accumulated_tool_calls.values())
+                    if accumulated_tool_calls
+                    else None
+                )
+
                 self._capture_streaming_event(
                     posthog_distinct_id,
                     posthog_trace_id,
@@ -321,8 +393,10 @@ class WrappedCompletions(openai.resources.chat.completions.Completions):
                     kwargs,
                     usage_stats,
                     latency,
-                    output,
-                    tools,
+                    accumulated_content,
+                    tool_calls_list,
+                    extract_available_tool_calls("openai", kwargs),
+                    model_from_response,
                 )
 
         return generator()
@@ -335,56 +409,57 @@ class WrappedCompletions(openai.resources.chat.completions.Completions):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
         output: Any,
         tool_calls: Optional[List[Dict[str, Any]]] = None,
+        available_tool_calls: Optional[List[Dict[str, Any]]] = None,
+        model_from_response: Optional[str] = None,
     ):
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        from posthog.ai.types import StreamingEventData
+        from posthog.ai.openai.openai_converter import (
+            format_openai_streaming_input,
+            format_openai_streaming_output,
+        )
+        from posthog.ai.utils import capture_streaming_event
 
-        event_properties = {
-            "$ai_provider": "openai",
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("messages")),
-            "$ai_output_choices": with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                [{"content": output, "role": "assistant"}],
-            ),
-            "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("prompt_tokens", 0),
-            "$ai_output_tokens": usage_stats.get("completion_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
-            "$ai_reasoning_tokens": usage_stats.get("reasoning_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(self._client.base_url),
-            **(posthog_properties or {}),
-        }
+        # Prepare standardized event data
+        formatted_input = format_openai_streaming_input(kwargs, "chat")
+        sanitized_input = sanitize_openai(formatted_input)
 
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                tool_calls,
-            )
+        # Use model from kwargs, fallback to model from response
+        model = kwargs.get("model") or model_from_response or "unknown"
 
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
+        event_data = StreamingEventData(
+            provider="openai",
+            model=model,
+            base_url=str(self._client.base_url),
+            kwargs=kwargs,
+            formatted_input=sanitized_input,
+            formatted_output=format_openai_streaming_output(output, "chat", tool_calls),
+            usage_stats=usage_stats,
+            latency=latency,
+            distinct_id=posthog_distinct_id,
+            trace_id=posthog_trace_id,
+            properties=posthog_properties,
+            privacy_mode=posthog_privacy_mode,
+            groups=posthog_groups,
+        )
 
-        if hasattr(self._client._ph_client, "capture"):
-            self._client._ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
-            )
+        # Use the common capture function
+        capture_streaming_event(self._client._ph_client, event_data)
 
 
-class WrappedEmbeddings(openai.resources.embeddings.Embeddings):
-    _client: OpenAI
+class WrappedEmbeddings:
+    """Wrapper for OpenAI embeddings that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_embeddings):
+        self._client = client
+        self._original = original_embeddings
+
+    def __getattr__(self, name):
+        """Fallback to original embeddings object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     def create(
         self,
@@ -402,16 +477,19 @@ class WrappedEmbeddings(openai.resources.embeddings.Embeddings):
             posthog_distinct_id: Optional ID to associate with the usage event.
             posthog_trace_id: Optional trace UUID for linking events.
             posthog_properties: Optional dictionary of extra properties to include in the event.
+            posthog_privacy_mode: Whether to anonymize the input and output.
+            posthog_groups: Optional dictionary of groups to associate with the event.
             **kwargs: Any additional parameters for the OpenAI Embeddings API.
 
         Returns:
             The response from OpenAI's embeddings.create call.
         """
+
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
         start_time = time.time()
-        response = super().create(**kwargs)
+        response = self._original.create(**kwargs)
         end_time = time.time()
 
         # Extract usage statistics if available
@@ -428,7 +506,11 @@ class WrappedEmbeddings(openai.resources.embeddings.Embeddings):
         event_properties = {
             "$ai_provider": "openai",
             "$ai_model": kwargs.get("model"),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("input")),
+            "$ai_input": with_privacy_mode(
+                self._client._ph_client,
+                posthog_privacy_mode,
+                sanitize_openai_response(kwargs.get("input")),
+            ),
             "$ai_http_status": 200,
             "$ai_input_tokens": usage_stats.get("prompt_tokens", 0),
             "$ai_latency": latency,
@@ -452,24 +534,48 @@ class WrappedEmbeddings(openai.resources.embeddings.Embeddings):
         return response
 
 
-class WrappedBeta(openai.resources.beta.Beta):
-    _client: OpenAI
+class WrappedBeta:
+    """Wrapper for OpenAI beta features that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_beta):
+        self._client = client
+        self._original = original_beta
+
+    def __getattr__(self, name):
+        """Fallback to original beta object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     @property
     def chat(self):
-        return WrappedBetaChat(self._client)
+        return WrappedBetaChat(self._client, self._original.chat)
 
 
-class WrappedBetaChat(openai.resources.beta.chat.Chat):
-    _client: OpenAI
+class WrappedBetaChat:
+    """Wrapper for OpenAI beta chat that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_beta_chat):
+        self._client = client
+        self._original = original_beta_chat
+
+    def __getattr__(self, name):
+        """Fallback to original beta chat object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     @property
     def completions(self):
-        return WrappedBetaCompletions(self._client)
+        return WrappedBetaCompletions(self._client, self._original.completions)
 
 
-class WrappedBetaCompletions(openai.resources.beta.chat.completions.Completions):
-    _client: OpenAI
+class WrappedBetaCompletions:
+    """Wrapper for OpenAI beta chat completions that tracks usage in PostHog."""
+
+    def __init__(self, client: OpenAI, original_beta_completions):
+        self._client = client
+        self._original = original_beta_completions
+
+    def __getattr__(self, name):
+        """Fallback to original beta completions object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     def parse(
         self,
@@ -489,6 +595,6 @@ class WrappedBetaCompletions(openai.resources.beta.chat.completions.Completions)
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().parse,
+            self._original.parse,
             **kwargs,
         )

posthog/ai/openai/openai_async.py

@@ -2,13 +2,31 @@ import time
 import uuid
 from typing import Any, Dict, List, Optional
 
+from posthog.ai.types import TokenUsage
+
 try:
     import openai
-    import openai.resources
 except ImportError:
-    raise ModuleNotFoundError("Please install the OpenAI SDK to use this feature: 'pip install openai'")
+    raise ModuleNotFoundError(
+        "Please install the OpenAI SDK to use this feature: 'pip install openai'"
+    )
 
-from posthog.ai.utils import call_llm_and_track_usage_async, get_model_params, with_privacy_mode
+from posthog import setup
+from posthog.ai.utils import (
+    call_llm_and_track_usage_async,
+    extract_available_tool_calls,
+    get_model_params,
+    merge_usage_stats,
+    with_privacy_mode,
+)
+from posthog.ai.openai.openai_converter import (
+    extract_openai_usage_from_chunk,
+    extract_openai_content_from_chunk,
+    extract_openai_tool_calls_from_chunk,
+    accumulate_openai_tool_calls,
+    format_openai_streaming_output,
+)
+from posthog.ai.sanitization import sanitize_openai, sanitize_openai_response
 from posthog.client import Client as PostHogClient
 
 
@@ -19,23 +37,49 @@ class AsyncOpenAI(openai.AsyncOpenAI):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
         """
         Args:
             api_key: OpenAI API key.
-            posthog_client: If provided, events will be captured via this client instance.
-            **openai_config: Additional keyword args (e.g. organization="xxx").
+            posthog_client: If provided, events will be captured via this client instead
+                            of the global posthog.
+            **openai_config: Any additional keyword args to set on openai (e.g. organization="xxx").
         """
+
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
-        self.chat = WrappedChat(self)
-        self.embeddings = WrappedEmbeddings(self)
-        self.beta = WrappedBeta(self)
-        self.responses = WrappedResponses(self)
+        self._ph_client = posthog_client or setup()
+
+        # Store original objects after parent initialization (only if they exist)
+        self._original_chat = getattr(self, "chat", None)
+        self._original_embeddings = getattr(self, "embeddings", None)
+        self._original_beta = getattr(self, "beta", None)
+        self._original_responses = getattr(self, "responses", None)
+
+        # Replace with wrapped versions (only if originals exist)
+        if self._original_chat is not None:
+            self.chat = WrappedChat(self, self._original_chat)
+
+        if self._original_embeddings is not None:
+            self.embeddings = WrappedEmbeddings(self, self._original_embeddings)
+
+        if self._original_beta is not None:
+            self.beta = WrappedBeta(self, self._original_beta)
+
+        if self._original_responses is not None:
+            self.responses = WrappedResponses(self, self._original_responses)
 
 
-class WrappedResponses(openai.resources.responses.Responses):
-    _client: AsyncOpenAI
+class WrappedResponses:
+    """Async wrapper for OpenAI responses that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_responses):
+        self._client = client
+        self._original = original_responses
+
+    def __getattr__(self, name):
+        """Fallback to original responses object for any methods we don't explicitly handle."""
+
+        return getattr(self._original, name)
 
     async def create(
         self,
@@ -68,7 +112,7 @@ class WrappedResponses(openai.resources.responses.Responses):
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().create,
+            self._original.create,
             **kwargs,
         )
 
@@ -82,41 +126,36 @@ class WrappedResponses(openai.resources.responses.Responses):
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {}
+        usage_stats: TokenUsage = TokenUsage()
         final_content = []
-        response = await super().create(**kwargs)
+        model_from_response: Optional[str] = None
+        response = await self._original.create(**kwargs)
 
         async def async_generator():
             nonlocal usage_stats
             nonlocal final_content  # noqa: F824
+            nonlocal model_from_response
 
             try:
                 async for chunk in response:
-                    if hasattr(chunk, "type") and chunk.type == "response.completed":
-                        res = chunk.response
-                        if res.output and len(res.output) > 0:
-                            final_content.append(res.output[0])
-
-                    if hasattr(chunk, "usage") and chunk.usage:
-                        usage_stats = {
-                            k: getattr(chunk.usage, k, 0)
-                            for k in [
-                                "input_tokens",
-                                "output_tokens",
-                                "total_tokens",
-                            ]
-                        }
-
-                        # Add support for cached tokens
-                        if hasattr(chunk.usage, "output_tokens_details") and hasattr(
-                            chunk.usage.output_tokens_details, "reasoning_tokens"
+                    # Extract model from response object in chunk (for stored prompts)
+                    if hasattr(chunk, "response") and chunk.response:
+                        if model_from_response is None and hasattr(
+                            chunk.response, "model"
                         ):
-                            usage_stats["reasoning_tokens"] = chunk.usage.output_tokens_details.reasoning_tokens
+                            model_from_response = chunk.response.model
 
-                        if hasattr(chunk.usage, "input_tokens_details") and hasattr(
-                            chunk.usage.input_tokens_details, "cached_tokens"
-                        ):
-                            usage_stats["cache_read_input_tokens"] = chunk.usage.input_tokens_details.cached_tokens
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_openai_usage_from_chunk(chunk, "responses")
+
+                    if chunk_usage:
+                        merge_usage_stats(usage_stats, chunk_usage)
+
+                    # Extract content from chunk
+                    content = extract_openai_content_from_chunk(chunk, "responses")
+
+                    if content is not None:
+                        final_content.append(content)
 
                     yield chunk
 
@@ -124,6 +163,7 @@ class WrappedResponses(openai.resources.responses.Responses):
                 end_time = time.time()
                 latency = end_time - start_time
                 output = final_content
+
                 await self._capture_streaming_event(
                     posthog_distinct_id,
                     posthog_trace_id,
@@ -134,6 +174,8 @@ class WrappedResponses(openai.resources.responses.Responses):
                     usage_stats,
                     latency,
                     output,
+                    extract_available_tool_calls("openai", kwargs),
+                    model_from_response,
                 )
 
         return async_generator()
@@ -146,28 +188,38 @@ class WrappedResponses(openai.resources.responses.Responses):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
         output: Any,
-        tool_calls: Optional[List[Dict[str, Any]]] = None,
+        available_tool_calls: Optional[List[Dict[str, Any]]] = None,
+        model_from_response: Optional[str] = None,
     ):
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
+        # Use model from kwargs, fallback to model from response
+        model = kwargs.get("model") or model_from_response or "unknown"
+
         event_properties = {
             "$ai_provider": "openai",
-            "$ai_model": kwargs.get("model"),
+            "$ai_model": model,
             "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("input")),
+            "$ai_input": with_privacy_mode(
+                self._client._ph_client,
+                posthog_privacy_mode,
+                sanitize_openai_response(kwargs.get("input")),
+            ),
             "$ai_output_choices": with_privacy_mode(
                 self._client._ph_client,
                 posthog_privacy_mode,
-                output,
+                format_openai_streaming_output(output, "responses"),
             ),
             "$ai_http_status": 200,
             "$ai_input_tokens": usage_stats.get("input_tokens", 0),
             "$ai_output_tokens": usage_stats.get("output_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
+            "$ai_cache_read_input_tokens": usage_stats.get(
+                "cache_read_input_tokens", 0
+            ),
             "$ai_reasoning_tokens": usage_stats.get("reasoning_tokens", 0),
             "$ai_latency": latency,
             "$ai_trace_id": posthog_trace_id,
@@ -175,35 +227,92 @@ class WrappedResponses(openai.resources.responses.Responses):
             **(posthog_properties or {}),
         }
 
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                tool_calls,
-            )
+        # Add web search count if present
+        web_search_count = usage_stats.get("web_search_count")
+        if (
+            web_search_count is not None
+            and isinstance(web_search_count, int)
+            and web_search_count > 0
+        ):
+            event_properties["$ai_web_search_count"] = web_search_count
+
+        if available_tool_calls:
+            event_properties["$ai_tools"] = available_tool_calls
 
         if posthog_distinct_id is None:
             event_properties["$process_person_profile"] = False
 
         if hasattr(self._client._ph_client, "capture"):
-            await self._client._ph_client.capture(
+            self._client._ph_client.capture(
                 distinct_id=posthog_distinct_id or posthog_trace_id,
                 event="$ai_generation",
                 properties=event_properties,
                 groups=posthog_groups,
             )
 
+    async def parse(
+        self,
+        posthog_distinct_id: Optional[str] = None,
+        posthog_trace_id: Optional[str] = None,
+        posthog_properties: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool = False,
+        posthog_groups: Optional[Dict[str, Any]] = None,
+        **kwargs: Any,
+    ):
+        """
+        Parse structured output using OpenAI's 'responses.parse' method, but also track usage in PostHog.
 
-class WrappedChat(openai.resources.chat.AsyncChat):
-    _client: AsyncOpenAI
+        Args:
+            posthog_distinct_id: Optional ID to associate with the usage event.
+            posthog_trace_id: Optional trace UUID for linking events.
+            posthog_properties: Optional dictionary of extra properties to include in the event.
+            posthog_privacy_mode: Whether to anonymize the input and output.
+            posthog_groups: Optional dictionary of groups to associate with the event.
+            **kwargs: Any additional parameters for the OpenAI Responses Parse API.
+
+        Returns:
+            The response from OpenAI's responses.parse call.
+        """
+        return await call_llm_and_track_usage_async(
+            posthog_distinct_id,
+            self._client._ph_client,
+            "openai",
+            posthog_trace_id,
+            posthog_properties,
+            posthog_privacy_mode,
+            posthog_groups,
+            self._client.base_url,
+            self._original.parse,
+            **kwargs,
+        )
+
+
+class WrappedChat:
+    """Async wrapper for OpenAI chat that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_chat):
+        self._client = client
+        self._original = original_chat
+
+    def __getattr__(self, name):
+        """Fallback to original chat object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     @property
     def completions(self):
-        return WrappedCompletions(self._client)
+        return WrappedCompletions(self._client, self._original.completions)
 
 
-class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
-    _client: AsyncOpenAI
+class WrappedCompletions:
+    """Async wrapper for OpenAI chat completions that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_completions):
+        self._client = client
+        self._original = original_completions
+
+    def __getattr__(self, name):
+        """Fallback to original completions object for any methods we don't explicitly handle."""
+        return getattr(self._original, name)
 
     async def create(
         self,
@@ -237,7 +346,7 @@ class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().create,
+            self._original.create,
             **kwargs,
         )
         return response
@@ -247,64 +356,63 @@ class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
         posthog_distinct_id: Optional[str],
         posthog_trace_id: Optional[str],
         posthog_properties: Optional[Dict[str, Any]],
-        posthog_privacy_mode: bool = False,
-        posthog_groups: Optional[Dict[str, Any]] = None,
+        posthog_privacy_mode: bool,
+        posthog_groups: Optional[Dict[str, Any]],
         **kwargs: Any,
     ):
         start_time = time.time()
-        usage_stats: Dict[str, int] = {}
+        usage_stats: TokenUsage = TokenUsage()
         accumulated_content = []
-        accumulated_tools = {}
+        accumulated_tool_calls: Dict[int, Dict[str, Any]] = {}
+        model_from_response: Optional[str] = None
+
         if "stream_options" not in kwargs:
             kwargs["stream_options"] = {}
         kwargs["stream_options"]["include_usage"] = True
-        response = await super().create(**kwargs)
+        response = await self._original.create(**kwargs)
 
         async def async_generator():
-            nonlocal usage_stats, accumulated_content, accumulated_tools  # noqa: F824
+            nonlocal usage_stats
+            nonlocal accumulated_content  # noqa: F824
+            nonlocal accumulated_tool_calls
+            nonlocal model_from_response
+
             try:
                 async for chunk in response:
-                    if hasattr(chunk, "usage") and chunk.usage:
-                        usage_stats = {
-                            k: getattr(chunk.usage, k, 0)
-                            for k in [
-                                "prompt_tokens",
-                                "completion_tokens",
-                                "total_tokens",
-                            ]
-                        }
+                    # Extract model from chunk (Chat Completions chunks have model field)
+                    if model_from_response is None and hasattr(chunk, "model"):
+                        model_from_response = chunk.model
 
-                        # Add support for cached tokens
-                        if hasattr(chunk.usage, "prompt_tokens_details") and hasattr(
-                            chunk.usage.prompt_tokens_details, "cached_tokens"
-                        ):
-                            usage_stats["cache_read_input_tokens"] = chunk.usage.prompt_tokens_details.cached_tokens
+                    # Extract usage stats from chunk
+                    chunk_usage = extract_openai_usage_from_chunk(chunk, "chat")
+                    if chunk_usage:
+                        merge_usage_stats(usage_stats, chunk_usage)
 
-                    if hasattr(chunk, "choices") and chunk.choices and len(chunk.choices) > 0:
-                        if chunk.choices[0].delta and chunk.choices[0].delta.content:
-                            content = chunk.choices[0].delta.content
-                            if content:
-                                accumulated_content.append(content)
+                    # Extract content from chunk
+                    content = extract_openai_content_from_chunk(chunk, "chat")
+                    if content is not None:
+                        accumulated_content.append(content)
 
-                        # Process tool calls
-                        tool_calls = getattr(chunk.choices[0].delta, "tool_calls", None)
-                        if tool_calls:
-                            for tool_call in tool_calls:
-                                index = tool_call.index
-                                if index not in accumulated_tools:
-                                    accumulated_tools[index] = tool_call
-                                else:
-                                    # Append arguments for existing tool calls
-                                    if hasattr(tool_call, "function") and hasattr(tool_call.function, "arguments"):
-                                        accumulated_tools[index].function.arguments += tool_call.function.arguments
+                    # Extract and accumulate tool calls from chunk
+                    chunk_tool_calls = extract_openai_tool_calls_from_chunk(chunk)
+                    if chunk_tool_calls:
+                        accumulate_openai_tool_calls(
+                            accumulated_tool_calls, chunk_tool_calls
+                        )
 
                     yield chunk
 
             finally:
                 end_time = time.time()
                 latency = end_time - start_time
-                output = "".join(accumulated_content)
-                tools = list(accumulated_tools.values()) if accumulated_tools else None
+
+                # Convert accumulated tool calls dict to list
+                tool_calls_list = (
+                    list(accumulated_tool_calls.values())
+                    if accumulated_tool_calls
+                    else None
+                )
+
                 await self._capture_streaming_event(
                     posthog_distinct_id,
                     posthog_trace_id,
@@ -314,8 +422,10 @@ class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
                     kwargs,
                     usage_stats,
                     latency,
-                    output,
-                    tools,
+                    accumulated_content,
+                    tool_calls_list,
+                    extract_available_tool_calls("openai", kwargs),
+                    model_from_response,
                 )
 
         return async_generator()
@@ -328,46 +438,64 @@ class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
         posthog_privacy_mode: bool,
         posthog_groups: Optional[Dict[str, Any]],
         kwargs: Dict[str, Any],
-        usage_stats: Dict[str, int],
+        usage_stats: TokenUsage,
         latency: float,
         output: Any,
         tool_calls: Optional[List[Dict[str, Any]]] = None,
+        available_tool_calls: Optional[List[Dict[str, Any]]] = None,
+        model_from_response: Optional[str] = None,
     ):
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
+        # Use model from kwargs, fallback to model from response
+        model = kwargs.get("model") or model_from_response or "unknown"
+
         event_properties = {
             "$ai_provider": "openai",
-            "$ai_model": kwargs.get("model"),
+            "$ai_model": model,
             "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("messages")),
+            "$ai_input": with_privacy_mode(
+                self._client._ph_client,
+                posthog_privacy_mode,
+                sanitize_openai(kwargs.get("messages")),
+            ),
             "$ai_output_choices": with_privacy_mode(
                 self._client._ph_client,
                 posthog_privacy_mode,
-                [{"content": output, "role": "assistant"}],
+                format_openai_streaming_output(output, "chat", tool_calls),
             ),
             "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("prompt_tokens", 0),
-            "$ai_output_tokens": usage_stats.get("completion_tokens", 0),
-            "$ai_cache_read_input_tokens": usage_stats.get("cache_read_input_tokens", 0),
+            "$ai_input_tokens": usage_stats.get("input_tokens", 0),
+            "$ai_output_tokens": usage_stats.get("output_tokens", 0),
+            "$ai_cache_read_input_tokens": usage_stats.get(
+                "cache_read_input_tokens", 0
+            ),
+            "$ai_reasoning_tokens": usage_stats.get("reasoning_tokens", 0),
             "$ai_latency": latency,
             "$ai_trace_id": posthog_trace_id,
             "$ai_base_url": str(self._client.base_url),
             **(posthog_properties or {}),
         }
 
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(
-                self._client._ph_client,
-                posthog_privacy_mode,
-                tool_calls,
-            )
+        # Add web search count if present
+        web_search_count = usage_stats.get("web_search_count")
+
+        if (
+            web_search_count is not None
+            and isinstance(web_search_count, int)
+            and web_search_count > 0
+        ):
+            event_properties["$ai_web_search_count"] = web_search_count
+
+        if available_tool_calls:
+            event_properties["$ai_tools"] = available_tool_calls
 
         if posthog_distinct_id is None:
             event_properties["$process_person_profile"] = False
 
         if hasattr(self._client._ph_client, "capture"):
-            await self._client._ph_client.capture(
+            self._client._ph_client.capture(
                 distinct_id=posthog_distinct_id or posthog_trace_id,
                 event="$ai_generation",
                 properties=event_properties,
@@ -375,8 +503,17 @@ class WrappedCompletions(openai.resources.chat.completions.AsyncCompletions):
             )
 
 
-class WrappedEmbeddings(openai.resources.embeddings.AsyncEmbeddings):
-    _client: AsyncOpenAI
+class WrappedEmbeddings:
+    """Async wrapper for OpenAI embeddings that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_embeddings):
+        self._client = client
+        self._original = original_embeddings
+
+    def __getattr__(self, name):
+        """Fallback to original embeddings object for any methods we don't explicitly handle."""
+
+        return getattr(self._original, name)
 
     async def create(
         self,
@@ -394,27 +531,29 @@ class WrappedEmbeddings(openai.resources.embeddings.AsyncEmbeddings):
             posthog_distinct_id: Optional ID to associate with the usage event.
             posthog_trace_id: Optional trace UUID for linking events.
             posthog_properties: Optional dictionary of extra properties to include in the event.
-            posthog_privacy_mode: Whether to store input and output in PostHog.
-            posthog_groups: Optional dictionary of groups to include in the event.
+            posthog_privacy_mode: Whether to anonymize the input and output.
+            posthog_groups: Optional dictionary of groups to associate with the event.
             **kwargs: Any additional parameters for the OpenAI Embeddings API.
 
         Returns:
             The response from OpenAI's embeddings.create call.
         """
+
         if posthog_trace_id is None:
             posthog_trace_id = str(uuid.uuid4())
 
         start_time = time.time()
-        response = await super().create(**kwargs)
+        response = await self._original.create(**kwargs)
         end_time = time.time()
 
         # Extract usage statistics if available
-        usage_stats = {}
+        usage_stats: TokenUsage = TokenUsage()
+
         if hasattr(response, "usage") and response.usage:
-            usage_stats = {
-                "prompt_tokens": getattr(response.usage, "prompt_tokens", 0),
-                "total_tokens": getattr(response.usage, "total_tokens", 0),
-            }
+            usage_stats = TokenUsage(
+                input_tokens=getattr(response.usage, "prompt_tokens", 0),
+                output_tokens=getattr(response.usage, "completion_tokens", 0),
+            )
 
         latency = end_time - start_time
 
@@ -422,9 +561,13 @@ class WrappedEmbeddings(openai.resources.embeddings.AsyncEmbeddings):
         event_properties = {
             "$ai_provider": "openai",
             "$ai_model": kwargs.get("model"),
-            "$ai_input": with_privacy_mode(self._client._ph_client, posthog_privacy_mode, kwargs.get("input")),
+            "$ai_input": with_privacy_mode(
+                self._client._ph_client,
+                posthog_privacy_mode,
+                sanitize_openai_response(kwargs.get("input")),
+            ),
             "$ai_http_status": 200,
-            "$ai_input_tokens": usage_stats.get("prompt_tokens", 0),
+            "$ai_input_tokens": usage_stats.get("input_tokens", 0),
             "$ai_latency": latency,
             "$ai_trace_id": posthog_trace_id,
             "$ai_base_url": str(self._client.base_url),
@@ -446,24 +589,51 @@ class WrappedEmbeddings(openai.resources.embeddings.AsyncEmbeddings):
         return response
 
 
-class WrappedBeta(openai.resources.beta.AsyncBeta):
-    _client: AsyncOpenAI
+class WrappedBeta:
+    """Async wrapper for OpenAI beta features that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_beta):
+        self._client = client
+        self._original = original_beta
+
+    def __getattr__(self, name):
+        """Fallback to original beta object for any methods we don't explicitly handle."""
+
+        return getattr(self._original, name)
 
     @property
     def chat(self):
-        return WrappedBetaChat(self._client)
+        return WrappedBetaChat(self._client, self._original.chat)
 
 
-class WrappedBetaChat(openai.resources.beta.chat.AsyncChat):
-    _client: AsyncOpenAI
+class WrappedBetaChat:
+    """Async wrapper for OpenAI beta chat that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_beta_chat):
+        self._client = client
+        self._original = original_beta_chat
+
+    def __getattr__(self, name):
+        """Fallback to original beta chat object for any methods we don't explicitly handle."""
+
+        return getattr(self._original, name)
 
     @property
     def completions(self):
-        return WrappedBetaCompletions(self._client)
+        return WrappedBetaCompletions(self._client, self._original.completions)
 
 
-class WrappedBetaCompletions(openai.resources.beta.chat.completions.AsyncCompletions):
-    _client: AsyncOpenAI
+class WrappedBetaCompletions:
+    """Async wrapper for OpenAI beta chat completions that tracks usage in PostHog."""
+
+    def __init__(self, client: AsyncOpenAI, original_beta_completions):
+        self._client = client
+        self._original = original_beta_completions
+
+    def __getattr__(self, name):
+        """Fallback to original beta completions object for any methods we don't explicitly handle."""
+
+        return getattr(self._original, name)
 
     async def parse(
         self,
@@ -483,6 +653,6 @@ class WrappedBetaCompletions(openai.resources.beta.chat.completions.AsyncComplet
             posthog_privacy_mode,
             posthog_groups,
             self._client.base_url,
-            super().parse,
+            self._original.parse,
             **kwargs,
         )

posthog/ai/openai/openai_converter.py

@@ -0,0 +1,741 @@
+"""
+OpenAI-specific conversion utilities.
+
+This module handles the conversion of OpenAI API responses and inputs
+into standardized formats for PostHog tracking. It supports both
+Chat Completions API and Responses API formats.
+"""
+
+from typing import Any, Dict, List, Optional
+
+from posthog.ai.types import (
+    FormattedContentItem,
+    FormattedFunctionCall,
+    FormattedImageContent,
+    FormattedMessage,
+    FormattedTextContent,
+    TokenUsage,
+)
+
+
+def format_openai_response(response: Any) -> List[FormattedMessage]:
+    """
+    Format an OpenAI response into standardized message format.
+
+    Handles both Chat Completions API and Responses API formats.
+
+    Args:
+        response: The response object from OpenAI API
+
+    Returns:
+        List of formatted messages with role and content
+    """
+
+    output: List[FormattedMessage] = []
+
+    if response is None:
+        return output
+
+    # Handle Chat Completions response format
+    if hasattr(response, "choices"):
+        content: List[FormattedContentItem] = []
+        role = "assistant"
+
+        for choice in response.choices:
+            if hasattr(choice, "message") and choice.message:
+                if choice.message.role:
+                    role = choice.message.role
+
+                if choice.message.content:
+                    content.append(
+                        {
+                            "type": "text",
+                            "text": choice.message.content,
+                        }
+                    )
+
+                if hasattr(choice.message, "tool_calls") and choice.message.tool_calls:
+                    for tool_call in choice.message.tool_calls:
+                        content.append(
+                            {
+                                "type": "function",
+                                "id": tool_call.id,
+                                "function": {
+                                    "name": tool_call.function.name,
+                                    "arguments": tool_call.function.arguments,
+                                },
+                            }
+                        )
+
+                # Handle audio output (gpt-4o-audio-preview)
+                if hasattr(choice.message, "audio") and choice.message.audio:
+                    # Convert Pydantic model to dict to capture all fields from OpenAI
+                    audio_dict = choice.message.audio.model_dump()
+                    content.append({"type": "audio", **audio_dict})
+
+        if content:
+            output.append(
+                {
+                    "role": role,
+                    "content": content,
+                }
+            )
+
+    # Handle Responses API format
+    if hasattr(response, "output"):
+        content = []
+        role = "assistant"
+
+        for item in response.output:
+            if item.type == "message":
+                role = item.role
+
+                if hasattr(item, "content") and isinstance(item.content, list):
+                    for content_item in item.content:
+                        if (
+                            hasattr(content_item, "type")
+                            and content_item.type == "output_text"
+                            and hasattr(content_item, "text")
+                        ):
+                            content.append(
+                                {
+                                    "type": "text",
+                                    "text": content_item.text,
+                                }
+                            )
+
+                        elif hasattr(content_item, "text"):
+                            content.append({"type": "text", "text": content_item.text})
+
+                        elif (
+                            hasattr(content_item, "type")
+                            and content_item.type == "input_image"
+                            and hasattr(content_item, "image_url")
+                        ):
+                            image_content: FormattedImageContent = {
+                                "type": "image",
+                                "image": content_item.image_url,
+                            }
+                            content.append(image_content)
+
+                elif hasattr(item, "content"):
+                    text_content = {"type": "text", "text": str(item.content)}
+                    content.append(text_content)
+
+            elif hasattr(item, "type") and item.type == "function_call":
+                content.append(
+                    {
+                        "type": "function",
+                        "id": getattr(item, "call_id", getattr(item, "id", "")),
+                        "function": {
+                            "name": item.name,
+                            "arguments": getattr(item, "arguments", {}),
+                        },
+                    }
+                )
+
+        if content:
+            output.append(
+                {
+                    "role": role,
+                    "content": content,
+                }
+            )
+
+    return output
+
+
+def format_openai_input(
+    messages: Optional[List[Dict[str, Any]]] = None, input_data: Optional[Any] = None
+) -> List[FormattedMessage]:
+    """
+    Format OpenAI input messages.
+
+    Handles both messages parameter (Chat Completions) and input parameter (Responses API).
+
+    Args:
+        messages: List of message dictionaries for Chat Completions API
+        input_data: Input data for Responses API
+
+    Returns:
+        List of formatted messages
+    """
+
+    formatted_messages: List[FormattedMessage] = []
+
+    # Handle Chat Completions API format
+    if messages is not None:
+        for msg in messages:
+            formatted_messages.append(
+                {
+                    "role": msg.get("role", "user"),
+                    "content": msg.get("content", ""),
+                }
+            )
+
+    # Handle Responses API format
+    if input_data is not None:
+        if isinstance(input_data, list):
+            for item in input_data:
+                role = "user"
+                content = ""
+
+                if isinstance(item, dict):
+                    role = item.get("role", "user")
+                    content = item.get("content", "")
+
+                elif isinstance(item, str):
+                    content = item
+
+                else:
+                    content = str(item)
+
+                formatted_messages.append({"role": role, "content": content})
+
+        elif isinstance(input_data, str):
+            formatted_messages.append({"role": "user", "content": input_data})
+
+        else:
+            formatted_messages.append({"role": "user", "content": str(input_data)})
+
+    return formatted_messages
+
+
+def extract_openai_tools(kwargs: Dict[str, Any]) -> Optional[Any]:
+    """
+    Extract tool definitions from OpenAI API kwargs.
+
+    Args:
+        kwargs: Keyword arguments passed to OpenAI API
+
+    Returns:
+        Tool definitions if present, None otherwise
+    """
+
+    # Check for tools parameter (newer API)
+    if "tools" in kwargs:
+        return kwargs["tools"]
+
+    # Check for functions parameter (older API)
+    if "functions" in kwargs:
+        return kwargs["functions"]
+
+    return None
+
+
+def format_openai_streaming_content(
+    accumulated_content: str, tool_calls: Optional[List[Dict[str, Any]]] = None
+) -> List[FormattedContentItem]:
+    """
+    Format content from OpenAI streaming response.
+
+    Used by streaming handlers to format accumulated content.
+
+    Args:
+        accumulated_content: Accumulated text content from streaming
+        tool_calls: Optional list of tool calls accumulated during streaming
+
+    Returns:
+        List of formatted content items
+    """
+    formatted: List[FormattedContentItem] = []
+
+    # Add text content if present
+    if accumulated_content:
+        text_content: FormattedTextContent = {
+            "type": "text",
+            "text": accumulated_content,
+        }
+        formatted.append(text_content)
+
+    # Add tool calls if present
+    if tool_calls:
+        for tool_call in tool_calls:
+            function_call: FormattedFunctionCall = {
+                "type": "function",
+                "id": tool_call.get("id"),
+                "function": tool_call.get("function", {}),
+            }
+            formatted.append(function_call)
+
+    return formatted
+
+
+def extract_openai_web_search_count(response: Any) -> int:
+    """
+    Extract web search count from OpenAI response.
+
+    Uses a two-tier detection strategy:
+    1. Priority 1 (exact count): Check for output[].type == "web_search_call" (Responses API)
+    2. Priority 2 (binary detection): Check for various web search indicators:
+       - Root-level citations, search_results, or usage.search_context_size (Perplexity)
+       - Annotations with type "url_citation" in choices/output (including delta for streaming)
+
+    Args:
+        response: The response from OpenAI API
+
+    Returns:
+        Number of web search requests (exact count or binary 1/0)
+    """
+
+    # Priority 1: Check for exact count in Responses API output
+    if hasattr(response, "output"):
+        web_search_count = 0
+
+        for item in response.output:
+            if hasattr(item, "type") and item.type == "web_search_call":
+                web_search_count += 1
+
+        web_search_count = max(0, web_search_count)
+
+        if web_search_count > 0:
+            return web_search_count
+
+    # Priority 2: Binary detection (returns 1 or 0)
+
+    # Check root-level indicators (Perplexity)
+    if hasattr(response, "citations"):
+        citations = getattr(response, "citations")
+
+        if citations and len(citations) > 0:
+            return 1
+
+    if hasattr(response, "search_results"):
+        search_results = getattr(response, "search_results")
+
+        if search_results and len(search_results) > 0:
+            return 1
+
+    if hasattr(response, "usage") and hasattr(response.usage, "search_context_size"):
+        if response.usage.search_context_size:
+            return 1
+
+    # Check for url_citation annotations in choices (Chat Completions)
+    if hasattr(response, "choices"):
+        for choice in response.choices:
+            # Check message.annotations (non-streaming or final chunk)
+            if hasattr(choice, "message") and hasattr(choice.message, "annotations"):
+                annotations = choice.message.annotations
+
+                if annotations:
+                    for annotation in annotations:
+                        # Support both dict and object formats
+                        annotation_type = (
+                            annotation.get("type")
+                            if isinstance(annotation, dict)
+                            else getattr(annotation, "type", None)
+                        )
+
+                        if annotation_type == "url_citation":
+                            return 1
+
+            # Check delta.annotations (streaming chunks)
+            if hasattr(choice, "delta") and hasattr(choice.delta, "annotations"):
+                annotations = choice.delta.annotations
+
+                if annotations:
+                    for annotation in annotations:
+                        # Support both dict and object formats
+                        annotation_type = (
+                            annotation.get("type")
+                            if isinstance(annotation, dict)
+                            else getattr(annotation, "type", None)
+                        )
+
+                        if annotation_type == "url_citation":
+                            return 1
+
+    # Check for url_citation annotations in output (Responses API)
+    if hasattr(response, "output"):
+        for item in response.output:
+            if hasattr(item, "content") and isinstance(item.content, list):
+                for content_item in item.content:
+                    if hasattr(content_item, "annotations"):
+                        annotations = content_item.annotations
+
+                        if annotations:
+                            for annotation in annotations:
+                                # Support both dict and object formats
+                                annotation_type = (
+                                    annotation.get("type")
+                                    if isinstance(annotation, dict)
+                                    else getattr(annotation, "type", None)
+                                )
+
+                                if annotation_type == "url_citation":
+                                    return 1
+
+    return 0
+
+
+def extract_openai_usage_from_response(response: Any) -> TokenUsage:
+    """
+    Extract usage statistics from a full OpenAI response (non-streaming).
+    Handles both Chat Completions and Responses API.
+
+    Args:
+        response: The complete response from OpenAI API
+
+    Returns:
+        TokenUsage with standardized usage statistics
+    """
+    if not hasattr(response, "usage"):
+        return TokenUsage(input_tokens=0, output_tokens=0)
+
+    cached_tokens = 0
+    input_tokens = 0
+    output_tokens = 0
+    reasoning_tokens = 0
+
+    # Responses API format
+    if hasattr(response.usage, "input_tokens"):
+        input_tokens = response.usage.input_tokens
+    if hasattr(response.usage, "output_tokens"):
+        output_tokens = response.usage.output_tokens
+    if hasattr(response.usage, "input_tokens_details") and hasattr(
+        response.usage.input_tokens_details, "cached_tokens"
+    ):
+        cached_tokens = response.usage.input_tokens_details.cached_tokens
+    if hasattr(response.usage, "output_tokens_details") and hasattr(
+        response.usage.output_tokens_details, "reasoning_tokens"
+    ):
+        reasoning_tokens = response.usage.output_tokens_details.reasoning_tokens
+
+    # Chat Completions format
+    if hasattr(response.usage, "prompt_tokens"):
+        input_tokens = response.usage.prompt_tokens
+    if hasattr(response.usage, "completion_tokens"):
+        output_tokens = response.usage.completion_tokens
+    if hasattr(response.usage, "prompt_tokens_details") and hasattr(
+        response.usage.prompt_tokens_details, "cached_tokens"
+    ):
+        cached_tokens = response.usage.prompt_tokens_details.cached_tokens
+    if hasattr(response.usage, "completion_tokens_details") and hasattr(
+        response.usage.completion_tokens_details, "reasoning_tokens"
+    ):
+        reasoning_tokens = response.usage.completion_tokens_details.reasoning_tokens
+
+    result = TokenUsage(
+        input_tokens=input_tokens,
+        output_tokens=output_tokens,
+    )
+
+    if cached_tokens > 0:
+        result["cache_read_input_tokens"] = cached_tokens
+    if reasoning_tokens > 0:
+        result["reasoning_tokens"] = reasoning_tokens
+
+    web_search_count = extract_openai_web_search_count(response)
+    if web_search_count > 0:
+        result["web_search_count"] = web_search_count
+
+    return result
+
+
+def extract_openai_usage_from_chunk(
+    chunk: Any, provider_type: str = "chat"
+) -> TokenUsage:
+    """
+    Extract usage statistics from an OpenAI streaming chunk.
+
+    Handles both Chat Completions and Responses API formats.
+
+    Args:
+        chunk: Streaming chunk from OpenAI API
+        provider_type: Either "chat" or "responses" to handle different API formats
+
+    Returns:
+        Dictionary of usage statistics
+    """
+
+    usage: TokenUsage = TokenUsage()
+
+    if provider_type == "chat":
+        # Extract web search count from the chunk before checking for usage
+        # Web search indicators (citations, annotations) can appear on any chunk,
+        # not just those with usage data
+        web_search_count = extract_openai_web_search_count(chunk)
+        if web_search_count > 0:
+            usage["web_search_count"] = web_search_count
+
+        if not hasattr(chunk, "usage") or not chunk.usage:
+            return usage
+
+        # Chat Completions API uses prompt_tokens and completion_tokens
+        # Standardize to input_tokens and output_tokens
+        usage["input_tokens"] = getattr(chunk.usage, "prompt_tokens", 0)
+        usage["output_tokens"] = getattr(chunk.usage, "completion_tokens", 0)
+
+        # Handle cached tokens
+        if hasattr(chunk.usage, "prompt_tokens_details") and hasattr(
+            chunk.usage.prompt_tokens_details, "cached_tokens"
+        ):
+            usage["cache_read_input_tokens"] = (
+                chunk.usage.prompt_tokens_details.cached_tokens
+            )
+
+        # Handle reasoning tokens
+        if hasattr(chunk.usage, "completion_tokens_details") and hasattr(
+            chunk.usage.completion_tokens_details, "reasoning_tokens"
+        ):
+            usage["reasoning_tokens"] = (
+                chunk.usage.completion_tokens_details.reasoning_tokens
+            )
+
+    elif provider_type == "responses":
+        # For Responses API, usage is only in chunk.response.usage for completed events
+        if hasattr(chunk, "type") and chunk.type == "response.completed":
+            if (
+                hasattr(chunk, "response")
+                and hasattr(chunk.response, "usage")
+                and chunk.response.usage
+            ):
+                response_usage = chunk.response.usage
+                usage["input_tokens"] = getattr(response_usage, "input_tokens", 0)
+                usage["output_tokens"] = getattr(response_usage, "output_tokens", 0)
+
+                # Handle cached tokens
+                if hasattr(response_usage, "input_tokens_details") and hasattr(
+                    response_usage.input_tokens_details, "cached_tokens"
+                ):
+                    usage["cache_read_input_tokens"] = (
+                        response_usage.input_tokens_details.cached_tokens
+                    )
+
+                # Handle reasoning tokens
+                if hasattr(response_usage, "output_tokens_details") and hasattr(
+                    response_usage.output_tokens_details, "reasoning_tokens"
+                ):
+                    usage["reasoning_tokens"] = (
+                        response_usage.output_tokens_details.reasoning_tokens
+                    )
+
+                # Extract web search count from the complete response
+                if hasattr(chunk, "response"):
+                    web_search_count = extract_openai_web_search_count(chunk.response)
+                    if web_search_count > 0:
+                        usage["web_search_count"] = web_search_count
+
+    return usage
+
+
+def extract_openai_content_from_chunk(
+    chunk: Any, provider_type: str = "chat"
+) -> Optional[str]:
+    """
+    Extract content from an OpenAI streaming chunk.
+
+    Handles both Chat Completions and Responses API formats.
+
+    Args:
+        chunk: Streaming chunk from OpenAI API
+        provider_type: Either "chat" or "responses" to handle different API formats
+
+    Returns:
+        Text content if present, None otherwise
+    """
+
+    if provider_type == "chat":
+        # Chat Completions API format
+        if (
+            hasattr(chunk, "choices")
+            and chunk.choices
+            and len(chunk.choices) > 0
+            and chunk.choices[0].delta
+            and chunk.choices[0].delta.content
+        ):
+            return chunk.choices[0].delta.content
+
+    elif provider_type == "responses":
+        # Responses API format
+        if hasattr(chunk, "type") and chunk.type == "response.completed":
+            if hasattr(chunk, "response") and chunk.response:
+                res = chunk.response
+                if res.output and len(res.output) > 0:
+                    # Return the full output for responses
+                    return res.output[0]
+
+    return None
+
+
+def extract_openai_tool_calls_from_chunk(chunk: Any) -> Optional[List[Dict[str, Any]]]:
+    """
+    Extract tool calls from an OpenAI streaming chunk.
+
+    Args:
+        chunk: Streaming chunk from OpenAI API
+
+    Returns:
+        List of tool call deltas if present, None otherwise
+    """
+    if (
+        hasattr(chunk, "choices")
+        and chunk.choices
+        and len(chunk.choices) > 0
+        and chunk.choices[0].delta
+        and hasattr(chunk.choices[0].delta, "tool_calls")
+        and chunk.choices[0].delta.tool_calls
+    ):
+        tool_calls = []
+        for tool_call in chunk.choices[0].delta.tool_calls:
+            tc_dict = {
+                "index": getattr(tool_call, "index", None),
+            }
+
+            if hasattr(tool_call, "id") and tool_call.id:
+                tc_dict["id"] = tool_call.id
+
+            if hasattr(tool_call, "type") and tool_call.type:
+                tc_dict["type"] = tool_call.type
+
+            if hasattr(tool_call, "function") and tool_call.function:
+                function_dict = {}
+                if hasattr(tool_call.function, "name") and tool_call.function.name:
+                    function_dict["name"] = tool_call.function.name
+                if (
+                    hasattr(tool_call.function, "arguments")
+                    and tool_call.function.arguments
+                ):
+                    function_dict["arguments"] = tool_call.function.arguments
+                tc_dict["function"] = function_dict
+
+            tool_calls.append(tc_dict)
+        return tool_calls
+
+    return None
+
+
+def accumulate_openai_tool_calls(
+    accumulated_tool_calls: Dict[int, Dict[str, Any]],
+    chunk_tool_calls: List[Dict[str, Any]],
+) -> None:
+    """
+    Accumulate tool calls from streaming chunks.
+
+    OpenAI sends tool calls incrementally:
+    - First chunk has id, type, function.name and partial function.arguments
+    - Subsequent chunks have more function.arguments
+
+    Args:
+        accumulated_tool_calls: Dictionary mapping index to accumulated tool call data
+        chunk_tool_calls: List of tool call deltas from current chunk
+    """
+    for tool_call_delta in chunk_tool_calls:
+        index = tool_call_delta.get("index")
+        if index is None:
+            continue
+
+        # Initialize tool call if first time seeing this index
+        if index not in accumulated_tool_calls:
+            accumulated_tool_calls[index] = {
+                "id": "",
+                "type": "function",
+                "function": {
+                    "name": "",
+                    "arguments": "",
+                },
+            }
+
+        # Update with new data from delta
+        tc = accumulated_tool_calls[index]
+
+        if "id" in tool_call_delta and tool_call_delta["id"]:
+            tc["id"] = tool_call_delta["id"]
+
+        if "type" in tool_call_delta and tool_call_delta["type"]:
+            tc["type"] = tool_call_delta["type"]
+
+        if "function" in tool_call_delta:
+            func_delta = tool_call_delta["function"]
+            if "name" in func_delta and func_delta["name"]:
+                tc["function"]["name"] = func_delta["name"]
+            if "arguments" in func_delta and func_delta["arguments"]:
+                # Arguments are sent incrementally, concatenate them
+                tc["function"]["arguments"] += func_delta["arguments"]
+
+
+def format_openai_streaming_output(
+    accumulated_content: Any,
+    provider_type: str = "chat",
+    tool_calls: Optional[List[Dict[str, Any]]] = None,
+) -> List[FormattedMessage]:
+    """
+    Format the final output from OpenAI streaming.
+
+    Args:
+        accumulated_content: Accumulated content from streaming (string for chat, list for responses)
+        provider_type: Either "chat" or "responses" to handle different API formats
+        tool_calls: Optional list of accumulated tool calls
+
+    Returns:
+        List of formatted messages
+    """
+
+    if provider_type == "chat":
+        content_items: List[FormattedContentItem] = []
+
+        # Add text content if present
+        if isinstance(accumulated_content, str) and accumulated_content:
+            content_items.append({"type": "text", "text": accumulated_content})
+        elif isinstance(accumulated_content, list):
+            # If it's a list of strings, join them
+            text = "".join(str(item) for item in accumulated_content if item)
+            if text:
+                content_items.append({"type": "text", "text": text})
+
+        # Add tool calls if present
+        if tool_calls:
+            for tool_call in tool_calls:
+                if "function" in tool_call:
+                    function_call: FormattedFunctionCall = {
+                        "type": "function",
+                        "id": tool_call.get("id", ""),
+                        "function": tool_call["function"],
+                    }
+                    content_items.append(function_call)
+
+        # Return formatted message with content
+        if content_items:
+            return [{"role": "assistant", "content": content_items}]
+        else:
+            # Empty response
+            return [{"role": "assistant", "content": []}]
+
+    elif provider_type == "responses":
+        # Responses API: accumulated_content is a list of output items
+        if isinstance(accumulated_content, list) and accumulated_content:
+            # The output is already formatted, just return it
+            return accumulated_content
+        elif isinstance(accumulated_content, str):
+            return [
+                {
+                    "role": "assistant",
+                    "content": [{"type": "text", "text": accumulated_content}],
+                }
+            ]
+
+    # Fallback for any other format
+    return [
+        {
+            "role": "assistant",
+            "content": [{"type": "text", "text": str(accumulated_content)}],
+        }
+    ]
+
+
+def format_openai_streaming_input(
+    kwargs: Dict[str, Any], api_type: str = "chat"
+) -> Any:
+    """
+    Format OpenAI streaming input based on API type.
+
+    Args:
+        kwargs: Keyword arguments passed to OpenAI API
+        api_type: Either "chat" or "responses"
+
+    Returns:
+        Formatted input ready for PostHog tracking
+    """
+    from posthog.ai.utils import merge_system_prompt
+
+    return merge_system_prompt(kwargs, "openai")

posthog/ai/openai/openai_providers.py

@@ -1,14 +1,24 @@
 try:
     import openai
-    import openai.resources
 except ImportError:
-    raise ModuleNotFoundError("Please install the Open AI SDK to use this feature: 'pip install openai'")
+    raise ModuleNotFoundError(
+        "Please install the Open AI SDK to use this feature: 'pip install openai'"
+    )
 
-from posthog.ai.openai.openai import WrappedBeta, WrappedChat, WrappedEmbeddings
+from posthog.ai.openai.openai import (
+    WrappedBeta,
+    WrappedChat,
+    WrappedEmbeddings,
+    WrappedResponses,
+)
 from posthog.ai.openai.openai_async import WrappedBeta as AsyncWrappedBeta
 from posthog.ai.openai.openai_async import WrappedChat as AsyncWrappedChat
 from posthog.ai.openai.openai_async import WrappedEmbeddings as AsyncWrappedEmbeddings
+from posthog.ai.openai.openai_async import WrappedResponses as AsyncWrappedResponses
+from typing import Optional
+
 from posthog.client import Client as PostHogClient
+from posthog import setup
 
 
 class AzureOpenAI(openai.AzureOpenAI):
@@ -18,24 +28,71 @@ class AzureOpenAI(openai.AzureOpenAI):
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
+        """
+        Args:
+            api_key: Azure OpenAI API key.
+            posthog_client: If provided, events will be captured via this client instead
+                            of the global posthog.
+            **openai_config: Any additional keyword args to set on Azure OpenAI (e.g. azure_endpoint="xxx").
+        """
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
-        self.chat = WrappedChat(self)
-        self.embeddings = WrappedEmbeddings(self)
-        self.beta = WrappedBeta(self)
+        self._ph_client = posthog_client or setup()
+
+        # Store original objects after parent initialization (only if they exist)
+        self._original_chat = getattr(self, "chat", None)
+        self._original_embeddings = getattr(self, "embeddings", None)
+        self._original_beta = getattr(self, "beta", None)
+        self._original_responses = getattr(self, "responses", None)
+
+        # Replace with wrapped versions (only if originals exist)
+        if self._original_chat is not None:
+            self.chat = WrappedChat(self, self._original_chat)
+
+        if self._original_embeddings is not None:
+            self.embeddings = WrappedEmbeddings(self, self._original_embeddings)
+
+        if self._original_beta is not None:
+            self.beta = WrappedBeta(self, self._original_beta)
+
+        if self._original_responses is not None:
+            self.responses = WrappedResponses(self, self._original_responses)
 
 
 class AsyncAzureOpenAI(openai.AsyncAzureOpenAI):
     """
-    A wrapper around the Azure OpenAI SDK that automatically sends LLM usage events to PostHog.
+    An async wrapper around the Azure OpenAI SDK that automatically sends LLM usage events to PostHog.
     """
 
     _ph_client: PostHogClient
 
-    def __init__(self, posthog_client: PostHogClient, **kwargs):
+    def __init__(self, posthog_client: Optional[PostHogClient] = None, **kwargs):
+        """
+        Args:
+            api_key: Azure OpenAI API key.
+            posthog_client: If provided, events will be captured via this client instead
+                            of the global posthog.
+            **openai_config: Any additional keyword args to set on Azure OpenAI (e.g. azure_endpoint="xxx").
+        """
         super().__init__(**kwargs)
-        self._ph_client = posthog_client
-        self.chat = AsyncWrappedChat(self)
-        self.embeddings = AsyncWrappedEmbeddings(self)
-        self.beta = AsyncWrappedBeta(self)
+        self._ph_client = posthog_client or setup()
+
+        # Store original objects after parent initialization (only if they exist)
+        self._original_chat = getattr(self, "chat", None)
+        self._original_embeddings = getattr(self, "embeddings", None)
+        self._original_beta = getattr(self, "beta", None)
+        self._original_responses = getattr(self, "responses", None)
+
+        # Replace with wrapped versions (only if originals exist)
+        if self._original_chat is not None:
+            self.chat = AsyncWrappedChat(self, self._original_chat)
+
+        if self._original_embeddings is not None:
+            self.embeddings = AsyncWrappedEmbeddings(self, self._original_embeddings)
+
+        if self._original_beta is not None:
+            self.beta = AsyncWrappedBeta(self, self._original_beta)
+
+        # Only add responses if available (newer OpenAI versions)
+        if self._original_responses is not None:
+            self.responses = AsyncWrappedResponses(self, self._original_responses)

posthog/ai/sanitization.py

@@ -0,0 +1,248 @@
+import os
+import re
+from typing import Any
+from urllib.parse import urlparse
+
+REDACTED_IMAGE_PLACEHOLDER = "[base64 image redacted]"
+
+
+def _is_multimodal_enabled() -> bool:
+    """Check if multimodal capture is enabled via environment variable."""
+    return os.environ.get("_INTERNAL_LLMA_MULTIMODAL", "").lower() in (
+        "true",
+        "1",
+        "yes",
+    )
+
+
+def is_base64_data_url(text: str) -> bool:
+    return re.match(r"^data:([^;]+);base64,", text) is not None
+
+
+def is_valid_url(text: str) -> bool:
+    try:
+        result = urlparse(text)
+        return bool(result.scheme and result.netloc)
+    except Exception:
+        pass
+
+    return text.startswith(("/", "./", "../"))
+
+
+def is_raw_base64(text: str) -> bool:
+    if is_valid_url(text):
+        return False
+
+    return len(text) > 20 and re.match(r"^[A-Za-z0-9+/]+=*$", text) is not None
+
+
+def redact_base64_data_url(value: Any) -> Any:
+    if _is_multimodal_enabled():
+        return value
+
+    if not isinstance(value, str):
+        return value
+
+    if is_base64_data_url(value):
+        return REDACTED_IMAGE_PLACEHOLDER
+
+    if is_raw_base64(value):
+        return REDACTED_IMAGE_PLACEHOLDER
+
+    return value
+
+
+def process_messages(messages: Any, transform_content_func) -> Any:
+    if not messages:
+        return messages
+
+    def process_content(content: Any) -> Any:
+        if isinstance(content, str):
+            return content
+
+        if not content:
+            return content
+
+        if isinstance(content, list):
+            return [transform_content_func(item) for item in content]
+
+        return transform_content_func(content)
+
+    def process_message(msg: Any) -> Any:
+        if not isinstance(msg, dict) or "content" not in msg:
+            return msg
+        return {**msg, "content": process_content(msg["content"])}
+
+    if isinstance(messages, list):
+        return [process_message(msg) for msg in messages]
+
+    return process_message(messages)
+
+
+def sanitize_openai_image(item: Any) -> Any:
+    if not isinstance(item, dict):
+        return item
+
+    if (
+        item.get("type") == "image_url"
+        and isinstance(item.get("image_url"), dict)
+        and "url" in item["image_url"]
+    ):
+        return {
+            **item,
+            "image_url": {
+                **item["image_url"],
+                "url": redact_base64_data_url(item["image_url"]["url"]),
+            },
+        }
+
+    if item.get("type") == "audio" and "data" in item:
+        if _is_multimodal_enabled():
+            return item
+        return {**item, "data": REDACTED_IMAGE_PLACEHOLDER}
+
+    return item
+
+
+def sanitize_openai_response_image(item: Any) -> Any:
+    if not isinstance(item, dict):
+        return item
+
+    if item.get("type") == "input_image" and "image_url" in item:
+        return {
+            **item,
+            "image_url": redact_base64_data_url(item["image_url"]),
+        }
+
+    return item
+
+
+def sanitize_anthropic_image(item: Any) -> Any:
+    if _is_multimodal_enabled():
+        return item
+
+    if not isinstance(item, dict):
+        return item
+
+    if (
+        item.get("type") == "image"
+        and isinstance(item.get("source"), dict)
+        and item["source"].get("type") == "base64"
+        and "data" in item["source"]
+    ):
+        return {
+            **item,
+            "source": {
+                **item["source"],
+                "data": REDACTED_IMAGE_PLACEHOLDER,
+            },
+        }
+
+    return item
+
+
+def sanitize_gemini_part(part: Any) -> Any:
+    if _is_multimodal_enabled():
+        return part
+
+    if not isinstance(part, dict):
+        return part
+
+    if (
+        "inline_data" in part
+        and isinstance(part["inline_data"], dict)
+        and "data" in part["inline_data"]
+    ):
+        return {
+            **part,
+            "inline_data": {
+                **part["inline_data"],
+                "data": REDACTED_IMAGE_PLACEHOLDER,
+            },
+        }
+
+    return part
+
+
+def process_gemini_item(item: Any) -> Any:
+    if not isinstance(item, dict):
+        return item
+
+    if "parts" in item and item["parts"]:
+        parts = item["parts"]
+        if isinstance(parts, list):
+            parts = [sanitize_gemini_part(part) for part in parts]
+        else:
+            parts = sanitize_gemini_part(parts)
+
+        return {**item, "parts": parts}
+
+    return item
+
+
+def sanitize_langchain_image(item: Any) -> Any:
+    if not isinstance(item, dict):
+        return item
+
+    if (
+        item.get("type") == "image_url"
+        and isinstance(item.get("image_url"), dict)
+        and "url" in item["image_url"]
+    ):
+        return {
+            **item,
+            "image_url": {
+                **item["image_url"],
+                "url": redact_base64_data_url(item["image_url"]["url"]),
+            },
+        }
+
+    if item.get("type") == "image" and "data" in item:
+        return {**item, "data": redact_base64_data_url(item["data"])}
+
+    if (
+        item.get("type") == "image"
+        and isinstance(item.get("source"), dict)
+        and "data" in item["source"]
+    ):
+        if _is_multimodal_enabled():
+            return item
+
+        return {
+            **item,
+            "source": {
+                **item["source"],
+                "data": REDACTED_IMAGE_PLACEHOLDER,
+            },
+        }
+
+    if item.get("type") == "media" and "data" in item:
+        return {**item, "data": redact_base64_data_url(item["data"])}
+
+    return item
+
+
+def sanitize_openai(data: Any) -> Any:
+    return process_messages(data, sanitize_openai_image)
+
+
+def sanitize_openai_response(data: Any) -> Any:
+    return process_messages(data, sanitize_openai_response_image)
+
+
+def sanitize_anthropic(data: Any) -> Any:
+    return process_messages(data, sanitize_anthropic_image)
+
+
+def sanitize_gemini(data: Any) -> Any:
+    if not data:
+        return data
+
+    if isinstance(data, list):
+        return [process_gemini_item(item) for item in data]
+
+    return process_gemini_item(data)
+
+
+def sanitize_langchain(data: Any) -> Any:
+    return process_messages(data, sanitize_langchain_image)

posthog/ai/types.py

@@ -0,0 +1,125 @@
+"""
+Common type definitions for PostHog AI SDK.
+
+These types are used for formatting messages and responses across different AI providers
+(Anthropic, OpenAI, Gemini, etc.) to ensure consistency in tracking and data structure.
+"""
+
+from typing import Any, Dict, List, Optional, TypedDict, Union
+
+
+class FormattedTextContent(TypedDict):
+    """Formatted text content item."""
+
+    type: str  # Literal["text"]
+    text: str
+
+
+class FormattedFunctionCall(TypedDict, total=False):
+    """Formatted function/tool call content item."""
+
+    type: str  # Literal["function"]
+    id: Optional[str]
+    function: Dict[str, Any]  # Contains 'name' and 'arguments'
+
+
+class FormattedImageContent(TypedDict):
+    """Formatted image content item."""
+
+    type: str  # Literal["image"]
+    image: str
+
+
+# Union type for all formatted content items
+FormattedContentItem = Union[
+    FormattedTextContent,
+    FormattedFunctionCall,
+    FormattedImageContent,
+    Dict[str, Any],  # Fallback for unknown content types
+]
+
+
+class FormattedMessage(TypedDict):
+    """
+    Standardized message format for PostHog tracking.
+
+    Used across all providers to ensure consistent message structure
+    when sending events to PostHog.
+    """
+
+    role: str
+    content: Union[str, List[FormattedContentItem], Any]
+
+
+class TokenUsage(TypedDict, total=False):
+    """
+    Token usage information for AI model responses.
+
+    Different providers may populate different fields.
+    """
+
+    input_tokens: int
+    output_tokens: int
+    cache_read_input_tokens: Optional[int]
+    cache_creation_input_tokens: Optional[int]
+    reasoning_tokens: Optional[int]
+    web_search_count: Optional[int]
+
+
+class ProviderResponse(TypedDict, total=False):
+    """
+    Standardized provider response format.
+
+    Used for consistent response formatting across all providers.
+    """
+
+    messages: List[FormattedMessage]
+    usage: TokenUsage
+    error: Optional[str]
+
+
+class StreamingContentBlock(TypedDict, total=False):
+    """
+    Content block used during streaming to accumulate content.
+
+    Used for tracking text and function calls as they stream in.
+    """
+
+    type: str  # "text" or "function"
+    text: Optional[str]
+    id: Optional[str]
+    function: Optional[Dict[str, Any]]
+
+
+class ToolInProgress(TypedDict):
+    """
+    Tracks a tool/function call being accumulated during streaming.
+
+    Used by Anthropic to accumulate JSON input for tools.
+    """
+
+    block: StreamingContentBlock
+    input_string: str
+
+
+class StreamingEventData(TypedDict):
+    """
+    Standardized data for streaming events across all providers.
+
+    This type ensures consistent data structure when capturing streaming events,
+    with all provider-specific formatting already completed.
+    """
+
+    provider: str  # "openai", "anthropic", "gemini"
+    model: str
+    base_url: str
+    kwargs: Dict[str, Any]  # Original kwargs for tool extraction and special handling
+    formatted_input: Any  # Provider-formatted input ready for tracking
+    formatted_output: Any  # Provider-formatted output ready for tracking
+    usage_stats: TokenUsage
+    latency: float
+    distinct_id: Optional[str]
+    trace_id: Optional[str]
+    properties: Optional[Dict[str, Any]]
+    privacy_mode: bool
+    groups: Optional[Dict[str, Any]]

posthog/ai/utils.py

@@ -1,12 +1,86 @@
 import time
 import uuid
-from typing import Any, Callable, Dict, List, Optional
-
-from httpx import URL
+from typing import Any, Callable, Dict, List, Optional, cast
 
+from posthog import get_tags, identify_context, new_context, tag
+from posthog.ai.sanitization import (
+    sanitize_anthropic,
+    sanitize_gemini,
+    sanitize_langchain,
+    sanitize_openai,
+)
+from posthog.ai.types import FormattedMessage, StreamingEventData, TokenUsage
 from posthog.client import Client as PostHogClient
 
 
+def merge_usage_stats(
+    target: TokenUsage, source: TokenUsage, mode: str = "incremental"
+) -> None:
+    """
+    Merge streaming usage statistics into target dict, handling None values.
+
+    Supports two modes:
+    - "incremental": Add source values to target (for APIs that report new tokens)
+    - "cumulative": Replace target with source values (for APIs that report totals)
+
+    Args:
+        target: Dictionary to update with usage stats
+        source: TokenUsage that may contain None values
+        mode: Either "incremental" or "cumulative"
+    """
+    if mode == "incremental":
+        # Add new values to existing totals
+        source_input = source.get("input_tokens")
+        if source_input is not None:
+            current = target.get("input_tokens") or 0
+            target["input_tokens"] = current + source_input
+
+        source_output = source.get("output_tokens")
+        if source_output is not None:
+            current = target.get("output_tokens") or 0
+            target["output_tokens"] = current + source_output
+
+        source_cache_read = source.get("cache_read_input_tokens")
+        if source_cache_read is not None:
+            current = target.get("cache_read_input_tokens") or 0
+            target["cache_read_input_tokens"] = current + source_cache_read
+
+        source_cache_creation = source.get("cache_creation_input_tokens")
+        if source_cache_creation is not None:
+            current = target.get("cache_creation_input_tokens") or 0
+            target["cache_creation_input_tokens"] = current + source_cache_creation
+
+        source_reasoning = source.get("reasoning_tokens")
+        if source_reasoning is not None:
+            current = target.get("reasoning_tokens") or 0
+            target["reasoning_tokens"] = current + source_reasoning
+
+        source_web_search = source.get("web_search_count")
+        if source_web_search is not None:
+            current = target.get("web_search_count") or 0
+            target["web_search_count"] = max(current, source_web_search)
+
+    elif mode == "cumulative":
+        # Replace with latest values (already cumulative)
+        if source.get("input_tokens") is not None:
+            target["input_tokens"] = source["input_tokens"]
+        if source.get("output_tokens") is not None:
+            target["output_tokens"] = source["output_tokens"]
+        if source.get("cache_read_input_tokens") is not None:
+            target["cache_read_input_tokens"] = source["cache_read_input_tokens"]
+        if source.get("cache_creation_input_tokens") is not None:
+            target["cache_creation_input_tokens"] = source[
+                "cache_creation_input_tokens"
+            ]
+        if source.get("reasoning_tokens") is not None:
+            target["reasoning_tokens"] = source["reasoning_tokens"]
+        if source.get("web_search_count") is not None:
+            target["web_search_count"] = source["web_search_count"]
+
+    else:
+        raise ValueError(f"Invalid mode: {mode}. Must be 'incremental' or 'cumulative'")
+
+
 def get_model_params(kwargs: Dict[str, Any]) -> Dict[str, Any]:
     """
     Extracts model parameters from the kwargs dictionary.
@@ -29,207 +103,135 @@ def get_model_params(kwargs: Dict[str, Any]) -> Dict[str, Any]:
     return model_params
 
 
-def get_usage(response, provider: str) -> Dict[str, Any]:
+def get_usage(response, provider: str) -> TokenUsage:
+    """
+    Extract usage statistics from response based on provider.
+    Delegates to provider-specific converter functions.
+    """
     if provider == "anthropic":
-        return {
-            "input_tokens": response.usage.input_tokens,
-            "output_tokens": response.usage.output_tokens,
-            "cache_read_input_tokens": response.usage.cache_read_input_tokens,
-            "cache_creation_input_tokens": response.usage.cache_creation_input_tokens,
-        }
+        from posthog.ai.anthropic.anthropic_converter import (
+            extract_anthropic_usage_from_response,
+        )
+
+        return extract_anthropic_usage_from_response(response)
     elif provider == "openai":
-        cached_tokens = 0
-        input_tokens = 0
-        output_tokens = 0
-        reasoning_tokens = 0
+        from posthog.ai.openai.openai_converter import (
+            extract_openai_usage_from_response,
+        )
 
-        # responses api
-        if hasattr(response.usage, "input_tokens"):
-            input_tokens = response.usage.input_tokens
-        if hasattr(response.usage, "output_tokens"):
-            output_tokens = response.usage.output_tokens
-        if hasattr(response.usage, "input_tokens_details") and hasattr(
-            response.usage.input_tokens_details, "cached_tokens"
-        ):
-            cached_tokens = response.usage.input_tokens_details.cached_tokens
-        if hasattr(response.usage, "output_tokens_details") and hasattr(
-            response.usage.output_tokens_details, "reasoning_tokens"
-        ):
-            reasoning_tokens = response.usage.output_tokens_details.reasoning_tokens
+        return extract_openai_usage_from_response(response)
+    elif provider == "gemini":
+        from posthog.ai.gemini.gemini_converter import (
+            extract_gemini_usage_from_response,
+        )
 
-        # chat completions
-        if hasattr(response.usage, "prompt_tokens"):
-            input_tokens = response.usage.prompt_tokens
-        if hasattr(response.usage, "completion_tokens"):
-            output_tokens = response.usage.completion_tokens
-        if hasattr(response.usage, "prompt_tokens_details") and hasattr(
-            response.usage.prompt_tokens_details, "cached_tokens"
-        ):
-            cached_tokens = response.usage.prompt_tokens_details.cached_tokens
+        return extract_gemini_usage_from_response(response)
 
-        return {
-            "input_tokens": input_tokens,
-            "output_tokens": output_tokens,
-            "cache_read_input_tokens": cached_tokens,
-            "reasoning_tokens": reasoning_tokens,
-        }
-    return {
-        "input_tokens": 0,
-        "output_tokens": 0,
-        "cache_read_input_tokens": 0,
-        "cache_creation_input_tokens": 0,
-        "reasoning_tokens": 0,
-    }
+    return TokenUsage(input_tokens=0, output_tokens=0)
 
 
 def format_response(response, provider: str):
     """
     Format a regular (non-streaming) response.
     """
-    output = []
-    if response is None:
-        return output
     if provider == "anthropic":
-        return format_response_anthropic(response)
+        from posthog.ai.anthropic.anthropic_converter import format_anthropic_response
+
+        return format_anthropic_response(response)
     elif provider == "openai":
-        return format_response_openai(response)
-    return output
+        from posthog.ai.openai.openai_converter import format_openai_response
+
+        return format_openai_response(response)
+    elif provider == "gemini":
+        from posthog.ai.gemini.gemini_converter import format_gemini_response
+
+        return format_gemini_response(response)
+    return []
 
 
-def format_response_anthropic(response):
-    output = []
-    for choice in response.content:
-        if choice.text:
-            output.append(
-                {
-                    "role": "assistant",
-                    "content": choice.text,
-                }
-            )
-    return output
-
-
-def format_response_openai(response):
-    output = []
-    if hasattr(response, "choices"):
-        for choice in response.choices:
-            # Handle Chat Completions response format
-            if hasattr(choice, "message") and choice.message and choice.message.content:
-                output.append(
-                    {
-                        "content": choice.message.content,
-                        "role": choice.message.role,
-                    }
-                )
-    # Handle Responses API format
-    if hasattr(response, "output"):
-        for item in response.output:
-            if item.type == "message":
-                # Extract text content from the content list
-                if hasattr(item, "content") and isinstance(item.content, list):
-                    for content_item in item.content:
-                        if (
-                            hasattr(content_item, "type")
-                            and content_item.type == "output_text"
-                            and hasattr(content_item, "text")
-                        ):
-                            output.append(
-                                {
-                                    "content": content_item.text,
-                                    "role": item.role,
-                                }
-                            )
-                        elif hasattr(content_item, "text"):
-                            output.append(
-                                {
-                                    "content": content_item.text,
-                                    "role": item.role,
-                                }
-                            )
-                        elif (
-                            hasattr(content_item, "type")
-                            and content_item.type == "input_image"
-                            and hasattr(content_item, "image_url")
-                        ):
-                            output.append(
-                                {
-                                    "content": {
-                                        "type": "image",
-                                        "image": content_item.image_url,
-                                    },
-                                    "role": item.role,
-                                }
-                            )
-                else:
-                    output.append(
-                        {
-                            "content": item.content,
-                            "role": item.role,
-                        }
-                    )
-    return output
-
-
-def format_tool_calls(response, provider: str):
+def extract_available_tool_calls(provider: str, kwargs: Dict[str, Any]):
+    """
+    Extract available tool calls for the given provider.
+    """
     if provider == "anthropic":
-        if hasattr(response, "tools") and response.tools and len(response.tools) > 0:
-            return response.tools
-    elif provider == "openai":
-        # Handle both Chat Completions and Responses API
-        if hasattr(response, "choices") and response.choices:
-            # Check for tool_calls in message (Chat Completions format)
-            if (
-                hasattr(response.choices[0], "message")
-                and hasattr(response.choices[0].message, "tool_calls")
-                and response.choices[0].message.tool_calls
-            ):
-                return response.choices[0].message.tool_calls
+        from posthog.ai.anthropic.anthropic_converter import extract_anthropic_tools
 
-            # Check for tool_calls directly in response (Responses API format)
-            if hasattr(response.choices[0], "tool_calls") and response.choices[0].tool_calls:
-                return response.choices[0].tool_calls
+        return extract_anthropic_tools(kwargs)
+    elif provider == "gemini":
+        from posthog.ai.gemini.gemini_converter import extract_gemini_tools
+
+        return extract_gemini_tools(kwargs)
+    elif provider == "openai":
+        from posthog.ai.openai.openai_converter import extract_openai_tools
+
+        return extract_openai_tools(kwargs)
     return None
 
 
-def merge_system_prompt(kwargs: Dict[str, Any], provider: str):
-    messages: List[Dict[str, Any]] = []
+def merge_system_prompt(
+    kwargs: Dict[str, Any], provider: str
+) -> List[FormattedMessage]:
+    """
+    Merge system prompts and format messages for the given provider.
+    """
     if provider == "anthropic":
+        from posthog.ai.anthropic.anthropic_converter import format_anthropic_input
+
         messages = kwargs.get("messages") or []
-        if kwargs.get("system") is None:
-            return messages
-        return [{"role": "system", "content": kwargs.get("system")}] + messages
+        system = kwargs.get("system")
+        return format_anthropic_input(messages, system)
+    elif provider == "gemini":
+        from posthog.ai.gemini.gemini_converter import format_gemini_input_with_system
 
-    # For OpenAI, handle both Chat Completions and Responses API
-    if kwargs.get("messages") is not None:
-        messages = list(kwargs.get("messages", []))
+        contents = kwargs.get("contents", [])
+        config = kwargs.get("config")
+        return format_gemini_input_with_system(contents, config)
+    elif provider == "openai":
+        from posthog.ai.openai.openai_converter import format_openai_input
 
-    if kwargs.get("input") is not None:
-        input_data = kwargs.get("input")
-        if isinstance(input_data, list):
-            messages.extend(input_data)
-        else:
-            messages.append({"role": "user", "content": input_data})
+        # For OpenAI, handle both Chat Completions and Responses API
+        messages_param = kwargs.get("messages")
+        input_param = kwargs.get("input")
 
-    # Check if system prompt is provided as a separate parameter
-    if kwargs.get("system") is not None:
-        has_system = any(msg.get("role") == "system" for msg in messages)
-        if not has_system:
-            messages = [{"role": "system", "content": kwargs.get("system")}] + messages
+        # Get base formatted messages
+        messages = format_openai_input(messages_param, input_param)
 
-    # For Responses API, add instructions to the system prompt if provided
-    if kwargs.get("instructions") is not None:
-        # Find the system message if it exists
-        system_idx = next((i for i, msg in enumerate(messages) if msg.get("role") == "system"), None)
+        # Check if system prompt is provided as a separate parameter
+        if kwargs.get("system") is not None:
+            has_system = any(msg.get("role") == "system" for msg in messages)
+            if not has_system:
+                system_msg = cast(
+                    FormattedMessage,
+                    {"role": "system", "content": kwargs.get("system")},
+                )
+                messages = [system_msg] + messages
 
-        if system_idx is not None:
-            # Append instructions to existing system message
-            system_content = messages[system_idx].get("content", "")
-            messages[system_idx]["content"] = f"{system_content}\n\n{kwargs.get('instructions')}"
-        else:
-            # Create a new system message with instructions
-            messages = [{"role": "system", "content": kwargs.get("instructions")}] + messages
+        # For Responses API, add instructions to the system prompt if provided
+        if kwargs.get("instructions") is not None:
+            # Find the system message if it exists
+            system_idx = next(
+                (i for i, msg in enumerate(messages) if msg.get("role") == "system"),
+                None,
+            )
 
-    return messages
+            if system_idx is not None:
+                # Append instructions to existing system message
+                system_content = messages[system_idx].get("content", "")
+                messages[system_idx]["content"] = (
+                    f"{system_content}\n\n{kwargs.get('instructions')}"
+                )
+            else:
+                # Create a new system message with instructions
+                instruction_msg = cast(
+                    FormattedMessage,
+                    {"role": "system", "content": kwargs.get("instructions")},
+                )
+                messages = [instruction_msg] + messages
+
+        return messages
+
+    # Default case - return empty list
+    return []
 
 
 def call_llm_and_track_usage(
@@ -240,7 +242,7 @@ def call_llm_and_track_usage(
     posthog_properties: Optional[Dict[str, Any]],
     posthog_privacy_mode: bool,
     posthog_groups: Optional[Dict[str, Any]],
-    base_url: URL,
+    base_url: str,
     call_method: Callable[..., Any],
     **kwargs: Any,
 ) -> Any:
@@ -252,81 +254,111 @@ def call_llm_and_track_usage(
     response = None
     error = None
     http_status = 200
-    usage: Dict[str, Any] = {}
-    error_params: Dict[str, any] = {}
+    usage: TokenUsage = TokenUsage()
+    error_params: Dict[str, Any] = {}
 
-    try:
-        response = call_method(**kwargs)
-    except Exception as exc:
-        error = exc
-        http_status = getattr(exc, "status_code", 0)  # default to 0 becuase its likely an SDK error
-        error_params = {
-            "$ai_is_error": True,
-            "$ai_error": exc.__str__(),
-        }
-    finally:
-        end_time = time.time()
-        latency = end_time - start_time
+    with new_context(client=ph_client, capture_exceptions=False):
+        if posthog_distinct_id:
+            identify_context(posthog_distinct_id)
 
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        try:
+            response = call_method(**kwargs)
+        except Exception as exc:
+            error = exc
+            http_status = getattr(
+                exc, "status_code", 0
+            )  # default to 0 becuase its likely an SDK error
+            error_params = {
+                "$ai_is_error": True,
+                "$ai_error": exc.__str__(),
+            }
+            # TODO: Add exception capture for OpenAI/Anthropic/Gemini wrappers when
+            # enable_exception_autocapture is True, similar to LangChain callbacks.
+            # See _capture_exception_and_update_properties in langchain/callbacks.py
+        finally:
+            end_time = time.time()
+            latency = end_time - start_time
 
-        if response and hasattr(response, "usage"):
-            usage = get_usage(response, provider)
+            if posthog_trace_id is None:
+                posthog_trace_id = str(uuid.uuid4())
 
-        messages = merge_system_prompt(kwargs, provider)
+            if response and (
+                hasattr(response, "usage")
+                or (provider == "gemini" and hasattr(response, "usage_metadata"))
+            ):
+                usage = get_usage(response, provider)
 
-        event_properties = {
-            "$ai_provider": provider,
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(ph_client, posthog_privacy_mode, messages),
-            "$ai_output_choices": with_privacy_mode(
-                ph_client, posthog_privacy_mode, format_response(response, provider)
-            ),
-            "$ai_http_status": http_status,
-            "$ai_input_tokens": usage.get("input_tokens", 0),
-            "$ai_output_tokens": usage.get("output_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(base_url),
-            **(posthog_properties or {}),
-            **(error_params or {}),
-        }
+            messages = merge_system_prompt(kwargs, provider)
+            sanitized_messages = sanitize_messages(messages, provider)
 
-        tool_calls = format_tool_calls(response, provider)
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(ph_client, posthog_privacy_mode, tool_calls)
-
-        if usage.get("cache_read_input_tokens") is not None and usage.get("cache_read_input_tokens", 0) > 0:
-            event_properties["$ai_cache_read_input_tokens"] = usage.get("cache_read_input_tokens", 0)
-
-        if usage.get("cache_creation_input_tokens") is not None and usage.get("cache_creation_input_tokens", 0) > 0:
-            event_properties["$ai_cache_creation_input_tokens"] = usage.get("cache_creation_input_tokens", 0)
-
-        if usage.get("reasoning_tokens") is not None and usage.get("reasoning_tokens", 0) > 0:
-            event_properties["$ai_reasoning_tokens"] = usage.get("reasoning_tokens", 0)
-
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
-
-        # Process instructions for Responses API
-        if provider == "openai" and kwargs.get("instructions") is not None:
-            event_properties["$ai_instructions"] = with_privacy_mode(
-                ph_client, posthog_privacy_mode, kwargs.get("instructions")
+            tag("$ai_provider", provider)
+            tag("$ai_model", kwargs.get("model") or getattr(response, "model", None))
+            tag("$ai_model_parameters", get_model_params(kwargs))
+            tag(
+                "$ai_input",
+                with_privacy_mode(ph_client, posthog_privacy_mode, sanitized_messages),
             )
-
-        # send the event to posthog
-        if hasattr(ph_client, "capture") and callable(ph_client.capture):
-            ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
+            tag(
+                "$ai_output_choices",
+                with_privacy_mode(
+                    ph_client, posthog_privacy_mode, format_response(response, provider)
+                ),
             )
+            tag("$ai_http_status", http_status)
+            tag("$ai_input_tokens", usage.get("input_tokens", 0))
+            tag("$ai_output_tokens", usage.get("output_tokens", 0))
+            tag("$ai_latency", latency)
+            tag("$ai_trace_id", posthog_trace_id)
+            tag("$ai_base_url", str(base_url))
 
-    if error:
-        raise error
+            available_tool_calls = extract_available_tool_calls(provider, kwargs)
+
+            if available_tool_calls:
+                tag("$ai_tools", available_tool_calls)
+
+            cache_read = usage.get("cache_read_input_tokens")
+            if cache_read is not None and cache_read > 0:
+                tag("$ai_cache_read_input_tokens", cache_read)
+
+            cache_creation = usage.get("cache_creation_input_tokens")
+            if cache_creation is not None and cache_creation > 0:
+                tag("$ai_cache_creation_input_tokens", cache_creation)
+
+            reasoning = usage.get("reasoning_tokens")
+            if reasoning is not None and reasoning > 0:
+                tag("$ai_reasoning_tokens", reasoning)
+
+            web_search_count = usage.get("web_search_count")
+            if web_search_count is not None and web_search_count > 0:
+                tag("$ai_web_search_count", web_search_count)
+
+            if posthog_distinct_id is None:
+                tag("$process_person_profile", False)
+
+            # Process instructions for Responses API
+            if provider == "openai" and kwargs.get("instructions") is not None:
+                tag(
+                    "$ai_instructions",
+                    with_privacy_mode(
+                        ph_client, posthog_privacy_mode, kwargs.get("instructions")
+                    ),
+                )
+
+            # send the event to posthog
+            if hasattr(ph_client, "capture") and callable(ph_client.capture):
+                ph_client.capture(
+                    distinct_id=posthog_distinct_id or posthog_trace_id,
+                    event="$ai_generation",
+                    properties={
+                        **get_tags(),
+                        **(posthog_properties or {}),
+                        **(error_params or {}),
+                    },
+                    groups=posthog_groups,
+                )
+
+        if error:
+            raise error
 
     return response
 
@@ -339,7 +371,7 @@ async def call_llm_and_track_usage_async(
     posthog_properties: Optional[Dict[str, Any]],
     posthog_privacy_mode: bool,
     posthog_groups: Optional[Dict[str, Any]],
-    base_url: URL,
+    base_url: str,
     call_async_method: Callable[..., Any],
     **kwargs: Any,
 ) -> Any:
@@ -347,83 +379,240 @@ async def call_llm_and_track_usage_async(
     response = None
     error = None
     http_status = 200
-    usage: Dict[str, Any] = {}
-    error_params: Dict[str, any] = {}
+    usage: TokenUsage = TokenUsage()
+    error_params: Dict[str, Any] = {}
 
-    try:
-        response = await call_async_method(**kwargs)
-    except Exception as exc:
-        error = exc
-        http_status = getattr(exc, "status_code", 0)  # default to 0 because its likely an SDK error
-        error_params = {
-            "$ai_is_error": True,
-            "$ai_error": exc.__str__(),
-        }
-    finally:
-        end_time = time.time()
-        latency = end_time - start_time
+    with new_context(client=ph_client, capture_exceptions=False):
+        if posthog_distinct_id:
+            identify_context(posthog_distinct_id)
 
-        if posthog_trace_id is None:
-            posthog_trace_id = str(uuid.uuid4())
+        try:
+            response = await call_async_method(**kwargs)
+        except Exception as exc:
+            error = exc
+            http_status = getattr(
+                exc, "status_code", 0
+            )  # default to 0 because its likely an SDK error
+            error_params = {
+                "$ai_is_error": True,
+                "$ai_error": exc.__str__(),
+            }
+            # TODO: Add exception capture for OpenAI/Anthropic/Gemini wrappers when
+            # enable_exception_autocapture is True, similar to LangChain callbacks.
+            # See _capture_exception_and_update_properties in langchain/callbacks.py
+        finally:
+            end_time = time.time()
+            latency = end_time - start_time
 
-        if response and hasattr(response, "usage"):
-            usage = get_usage(response, provider)
+            if posthog_trace_id is None:
+                posthog_trace_id = str(uuid.uuid4())
 
-        messages = merge_system_prompt(kwargs, provider)
+            if response and (
+                hasattr(response, "usage")
+                or (provider == "gemini" and hasattr(response, "usage_metadata"))
+            ):
+                usage = get_usage(response, provider)
 
-        event_properties = {
-            "$ai_provider": provider,
-            "$ai_model": kwargs.get("model"),
-            "$ai_model_parameters": get_model_params(kwargs),
-            "$ai_input": with_privacy_mode(ph_client, posthog_privacy_mode, messages),
-            "$ai_output_choices": with_privacy_mode(
-                ph_client, posthog_privacy_mode, format_response(response, provider)
-            ),
-            "$ai_http_status": http_status,
-            "$ai_input_tokens": usage.get("input_tokens", 0),
-            "$ai_output_tokens": usage.get("output_tokens", 0),
-            "$ai_latency": latency,
-            "$ai_trace_id": posthog_trace_id,
-            "$ai_base_url": str(base_url),
-            **(posthog_properties or {}),
-            **(error_params or {}),
-        }
+            messages = merge_system_prompt(kwargs, provider)
+            sanitized_messages = sanitize_messages(messages, provider)
 
-        tool_calls = format_tool_calls(response, provider)
-        if tool_calls:
-            event_properties["$ai_tools"] = with_privacy_mode(ph_client, posthog_privacy_mode, tool_calls)
-
-        if usage.get("cache_read_input_tokens") is not None and usage.get("cache_read_input_tokens", 0) > 0:
-            event_properties["$ai_cache_read_input_tokens"] = usage.get("cache_read_input_tokens", 0)
-
-        if usage.get("cache_creation_input_tokens") is not None and usage.get("cache_creation_input_tokens", 0) > 0:
-            event_properties["$ai_cache_creation_input_tokens"] = usage.get("cache_creation_input_tokens", 0)
-
-        if posthog_distinct_id is None:
-            event_properties["$process_person_profile"] = False
-
-        # Process instructions for Responses API
-        if provider == "openai" and kwargs.get("instructions") is not None:
-            event_properties["$ai_instructions"] = with_privacy_mode(
-                ph_client, posthog_privacy_mode, kwargs.get("instructions")
+            tag("$ai_provider", provider)
+            tag("$ai_model", kwargs.get("model") or getattr(response, "model", None))
+            tag("$ai_model_parameters", get_model_params(kwargs))
+            tag(
+                "$ai_input",
+                with_privacy_mode(ph_client, posthog_privacy_mode, sanitized_messages),
             )
-
-        # send the event to posthog
-        if hasattr(ph_client, "capture") and callable(ph_client.capture):
-            ph_client.capture(
-                distinct_id=posthog_distinct_id or posthog_trace_id,
-                event="$ai_generation",
-                properties=event_properties,
-                groups=posthog_groups,
+            tag(
+                "$ai_output_choices",
+                with_privacy_mode(
+                    ph_client, posthog_privacy_mode, format_response(response, provider)
+                ),
             )
+            tag("$ai_http_status", http_status)
+            tag("$ai_input_tokens", usage.get("input_tokens", 0))
+            tag("$ai_output_tokens", usage.get("output_tokens", 0))
+            tag("$ai_latency", latency)
+            tag("$ai_trace_id", posthog_trace_id)
+            tag("$ai_base_url", str(base_url))
 
-    if error:
-        raise error
+            available_tool_calls = extract_available_tool_calls(provider, kwargs)
+
+            if available_tool_calls:
+                tag("$ai_tools", available_tool_calls)
+
+            cache_read = usage.get("cache_read_input_tokens")
+            if cache_read is not None and cache_read > 0:
+                tag("$ai_cache_read_input_tokens", cache_read)
+
+            cache_creation = usage.get("cache_creation_input_tokens")
+            if cache_creation is not None and cache_creation > 0:
+                tag("$ai_cache_creation_input_tokens", cache_creation)
+
+            reasoning = usage.get("reasoning_tokens")
+            if reasoning is not None and reasoning > 0:
+                tag("$ai_reasoning_tokens", reasoning)
+
+            web_search_count = usage.get("web_search_count")
+            if web_search_count is not None and web_search_count > 0:
+                tag("$ai_web_search_count", web_search_count)
+
+            if posthog_distinct_id is None:
+                tag("$process_person_profile", False)
+
+            # Process instructions for Responses API
+            if provider == "openai" and kwargs.get("instructions") is not None:
+                tag(
+                    "$ai_instructions",
+                    with_privacy_mode(
+                        ph_client, posthog_privacy_mode, kwargs.get("instructions")
+                    ),
+                )
+
+            # send the event to posthog
+            if hasattr(ph_client, "capture") and callable(ph_client.capture):
+                ph_client.capture(
+                    distinct_id=posthog_distinct_id or posthog_trace_id,
+                    event="$ai_generation",
+                    properties={
+                        **get_tags(),
+                        **(posthog_properties or {}),
+                        **(error_params or {}),
+                    },
+                    groups=posthog_groups,
+                )
+
+        if error:
+            raise error
 
     return response
 
 
+def sanitize_messages(data: Any, provider: str) -> Any:
+    """Sanitize messages using provider-specific sanitization functions."""
+    if provider == "anthropic":
+        return sanitize_anthropic(data)
+    elif provider == "openai":
+        return sanitize_openai(data)
+    elif provider == "gemini":
+        return sanitize_gemini(data)
+    elif provider == "langchain":
+        return sanitize_langchain(data)
+    return data
+
+
 def with_privacy_mode(ph_client: PostHogClient, privacy_mode: bool, value: Any):
     if ph_client.privacy_mode or privacy_mode:
         return None
     return value
+
+
+def capture_streaming_event(
+    ph_client: PostHogClient,
+    event_data: StreamingEventData,
+):
+    """
+    Unified streaming event capture for all LLM providers.
+
+    This function handles the common logic for capturing streaming events across all providers.
+    All provider-specific formatting should be done BEFORE calling this function.
+
+    The function handles:
+    - Building PostHog event properties
+    - Extracting and adding tools based on provider
+    - Applying privacy mode
+    - Adding special token fields (cache, reasoning)
+    - Provider-specific fields (e.g., OpenAI instructions)
+    - Sending the event to PostHog
+
+    Args:
+        ph_client: PostHog client instance
+        event_data: Standardized streaming event data containing all necessary information
+    """
+    trace_id = event_data.get("trace_id") or str(uuid.uuid4())
+
+    # Build base event properties
+    event_properties = {
+        "$ai_provider": event_data["provider"],
+        "$ai_model": event_data["model"],
+        "$ai_model_parameters": get_model_params(event_data["kwargs"]),
+        "$ai_input": with_privacy_mode(
+            ph_client,
+            event_data["privacy_mode"],
+            event_data["formatted_input"],
+        ),
+        "$ai_output_choices": with_privacy_mode(
+            ph_client,
+            event_data["privacy_mode"],
+            event_data["formatted_output"],
+        ),
+        "$ai_http_status": 200,
+        "$ai_input_tokens": event_data["usage_stats"].get("input_tokens", 0),
+        "$ai_output_tokens": event_data["usage_stats"].get("output_tokens", 0),
+        "$ai_latency": event_data["latency"],
+        "$ai_trace_id": trace_id,
+        "$ai_base_url": str(event_data["base_url"]),
+        **(event_data.get("properties") or {}),
+    }
+
+    # Extract and add tools based on provider
+    available_tools = extract_available_tool_calls(
+        event_data["provider"],
+        event_data["kwargs"],
+    )
+    if available_tools:
+        event_properties["$ai_tools"] = available_tools
+
+    # Add optional token fields
+    # For Anthropic, always include cache fields even if 0 (backward compatibility)
+    # For others, only include if present and non-zero
+    if event_data["provider"] == "anthropic":
+        # Anthropic always includes cache fields
+        cache_read = event_data["usage_stats"].get("cache_read_input_tokens", 0)
+        cache_creation = event_data["usage_stats"].get("cache_creation_input_tokens", 0)
+        event_properties["$ai_cache_read_input_tokens"] = cache_read
+        event_properties["$ai_cache_creation_input_tokens"] = cache_creation
+    else:
+        # Other providers only include if non-zero
+        optional_token_fields = [
+            "cache_read_input_tokens",
+            "cache_creation_input_tokens",
+            "reasoning_tokens",
+        ]
+
+        for field in optional_token_fields:
+            value = event_data["usage_stats"].get(field)
+            if value is not None and isinstance(value, int) and value > 0:
+                event_properties[f"$ai_{field}"] = value
+
+    # Add web search count if present (all providers)
+    web_search_count = event_data["usage_stats"].get("web_search_count")
+    if (
+        web_search_count is not None
+        and isinstance(web_search_count, int)
+        and web_search_count > 0
+    ):
+        event_properties["$ai_web_search_count"] = web_search_count
+
+    # Handle provider-specific fields
+    if (
+        event_data["provider"] == "openai"
+        and event_data["kwargs"].get("instructions") is not None
+    ):
+        event_properties["$ai_instructions"] = with_privacy_mode(
+            ph_client,
+            event_data["privacy_mode"],
+            event_data["kwargs"]["instructions"],
+        )
+
+    if event_data.get("distinct_id") is None:
+        event_properties["$process_person_profile"] = False
+
+    # Send event to PostHog
+    if hasattr(ph_client, "capture"):
+        ph_client.capture(
+            distinct_id=event_data.get("distinct_id") or trace_id,
+            event="$ai_generation",
+            properties=event_properties,
+            groups=event_data.get("groups"),
+        )

posthog/args.py

@@ -0,0 +1,71 @@
+from typing import TypedDict, Optional, Any, Dict, Union, Tuple, Type
+from types import TracebackType
+from typing_extensions import NotRequired  # For Python < 3.11 compatibility
+from datetime import datetime
+import numbers
+from uuid import UUID
+
+from posthog.types import SendFeatureFlagsOptions
+
+ID_TYPES = Union[numbers.Number, str, UUID, int]
+
+
+class OptionalCaptureArgs(TypedDict):
+    """Optional arguments for the capture method.
+
+    Args:
+        distinct_id: Unique identifier for the person associated with this event. If not set, the context
+            distinct_id is used, if available, otherwise a UUID is generated, and the event is marked
+            as personless. Setting context-level distinct_id's is recommended.
+        properties: Dictionary of properties to track with the event
+        timestamp: When the event occurred (defaults to current time)
+        uuid: Unique identifier for this specific event. If not provided, one is generated. The event
+            UUID is returned, so you can correlate it with actions in your app (like showing users an
+            error ID if you capture an exception).
+        groups: Group identifiers to associate with this event (format: {group_type: group_key})
+        send_feature_flags: Whether to include currently active feature flags in the event properties.
+            Can be a boolean (True/False) or a SendFeatureFlagsOptions object for advanced configuration.
+            Defaults to False.
+        disable_geoip: Whether to disable GeoIP lookup for this event. Defaults to False.
+    """
+
+    distinct_id: NotRequired[Optional[ID_TYPES]]
+    properties: NotRequired[Optional[Dict[str, Any]]]
+    timestamp: NotRequired[Optional[Union[datetime, str]]]
+    uuid: NotRequired[Optional[str]]
+    groups: NotRequired[Optional[Dict[str, str]]]
+    send_feature_flags: NotRequired[
+        Optional[Union[bool, SendFeatureFlagsOptions]]
+    ]  # Updated to support both boolean and options object
+    disable_geoip: NotRequired[
+        Optional[bool]
+    ]  # As above, optional so we can tell if the user is intentionally overriding a client setting or not
+
+
+class OptionalSetArgs(TypedDict):
+    """Optional arguments for the set method.
+
+    Args:
+        distinct_id: Unique identifier for the user to set properties on. If not set, the context
+            distinct_id is used, if available, otherwise this function does nothing. Setting
+            context-level distinct_id's is recommended.
+        properties: Dictionary of properties to set on the person
+        timestamp: When the properties were set (defaults to current time)
+        uuid: Unique identifier for this operation. If not provided, one is generated. This
+            UUID is returned, so you can correlate it with actions in your app.
+        disable_geoip: Whether to disable GeoIP lookup for this operation. Defaults to False.
+    """
+
+    distinct_id: NotRequired[Optional[ID_TYPES]]
+    properties: NotRequired[Optional[Dict[str, Any]]]
+    timestamp: NotRequired[Optional[Union[datetime, str]]]
+    uuid: NotRequired[Optional[str]]
+    disable_geoip: NotRequired[Optional[bool]]
+
+
+ExcInfo = Union[
+    Tuple[Type[BaseException], BaseException, Optional[TracebackType]],
+    Tuple[None, None, None],
+]
+
+ExceptionArg = Union[BaseException, ExcInfo]

posthog/consumer.py

@@ -1,9 +1,9 @@
 import json
 import logging
+import time
 from threading import Thread
 
 import backoff
-import monotonic
 
 from posthog.request import APIError, DatetimeSerializer, batch_post
 
@@ -84,30 +84,36 @@ class Consumer(Thread):
             self.log.error("error uploading: %s", e)
             success = False
             if self.on_error:
-                self.on_error(e, batch)
+                try:
+                    self.on_error(e, batch)
+                except Exception as e:
+                    self.log.error("on_error handler failed: %s", e)
         finally:
             # mark items as acknowledged from queue
             for item in batch:
                 self.queue.task_done()
-            return success
+
+        return success
 
     def next(self):
         """Return the next batch of items to upload."""
         queue = self.queue
         items = []
 
-        start_time = monotonic.monotonic()
+        start_time = time.monotonic()
         total_size = 0
 
         while len(items) < self.flush_at:
-            elapsed = monotonic.monotonic() - start_time
+            elapsed = time.monotonic() - start_time
             if elapsed >= self.flush_interval:
                 break
             try:
                 item = queue.get(block=True, timeout=self.flush_interval - elapsed)
                 item_size = len(json.dumps(item, cls=DatetimeSerializer).encode())
                 if item_size > MAX_MSG_SIZE:
-                    self.log.error("Item exceeds 900kib limit, dropping. (%s)", str(item))
+                    self.log.error(
+                        "Item exceeds 900kib limit, dropping. (%s)", str(item)
+                    )
                     continue
                 items.append(item)
                 total_size += item_size
@@ -134,7 +140,9 @@ class Consumer(Thread):
                 # retry on all other errors (eg. network)
                 return False
 
-        @backoff.on_exception(backoff.expo, Exception, max_tries=self.retries + 1, giveup=fatal_exception)
+        @backoff.on_exception(
+            backoff.expo, Exception, max_tries=self.retries + 1, giveup=fatal_exception
+        )
         def send_request():
             batch_post(
                 self.api_key,

posthog/contexts.py

@@ -0,0 +1,408 @@
+import contextvars
+from contextlib import contextmanager
+from typing import Optional, Any, Callable, Dict, TypeVar, cast, TYPE_CHECKING
+
+if TYPE_CHECKING:
+    # To avoid circular imports
+    from posthog.client import Client
+
+
+class ContextScope:
+    def __init__(
+        self,
+        parent=None,
+        fresh: bool = False,
+        capture_exceptions: bool = True,
+        client: Optional["Client"] = None,
+    ):
+        self.client: Optional[Client] = client
+        self.parent = parent
+        self.fresh = fresh
+        self.capture_exceptions = capture_exceptions
+        self.session_id: Optional[str] = None
+        self.distinct_id: Optional[str] = None
+        self.device_id: Optional[str] = None
+        self.tags: Dict[str, Any] = {}
+        self.capture_exception_code_variables: Optional[bool] = None
+        self.code_variables_mask_patterns: Optional[list] = None
+        self.code_variables_ignore_patterns: Optional[list] = None
+
+    def set_session_id(self, session_id: str):
+        self.session_id = session_id
+
+    def set_distinct_id(self, distinct_id: str):
+        self.distinct_id = distinct_id
+
+    def set_device_id(self, device_id: str):
+        self.device_id = device_id
+
+    def add_tag(self, key: str, value: Any):
+        self.tags[key] = value
+
+    def set_capture_exception_code_variables(self, enabled: bool):
+        self.capture_exception_code_variables = enabled
+
+    def set_code_variables_mask_patterns(self, mask_patterns: list):
+        self.code_variables_mask_patterns = mask_patterns
+
+    def set_code_variables_ignore_patterns(self, ignore_patterns: list):
+        self.code_variables_ignore_patterns = ignore_patterns
+
+    def get_parent(self):
+        return self.parent
+
+    def get_session_id(self) -> Optional[str]:
+        if self.session_id is not None:
+            return self.session_id
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_session_id()
+        return None
+
+    def get_distinct_id(self) -> Optional[str]:
+        if self.distinct_id is not None:
+            return self.distinct_id
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_distinct_id()
+        return None
+
+    def get_device_id(self) -> Optional[str]:
+        if self.device_id is not None:
+            return self.device_id
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_device_id()
+        return None
+
+    def collect_tags(self) -> Dict[str, Any]:
+        if self.parent and not self.fresh:
+            # We want child tags to take precedence over parent tags,
+            # so collect parent tags first, then update with child tags.
+            tags = self.parent.collect_tags()
+            tags.update(self.tags)
+            return tags
+        return self.tags.copy()
+
+    def get_capture_exception_code_variables(self) -> Optional[bool]:
+        if self.capture_exception_code_variables is not None:
+            return self.capture_exception_code_variables
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_capture_exception_code_variables()
+        return None
+
+    def get_code_variables_mask_patterns(self) -> Optional[list]:
+        if self.code_variables_mask_patterns is not None:
+            return self.code_variables_mask_patterns
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_code_variables_mask_patterns()
+        return None
+
+    def get_code_variables_ignore_patterns(self) -> Optional[list]:
+        if self.code_variables_ignore_patterns is not None:
+            return self.code_variables_ignore_patterns
+        if self.parent is not None and not self.fresh:
+            return self.parent.get_code_variables_ignore_patterns()
+        return None
+
+
+_context_stack: contextvars.ContextVar[Optional[ContextScope]] = contextvars.ContextVar(
+    "posthog_context_stack", default=None
+)
+
+
+def _get_current_context() -> Optional[ContextScope]:
+    return _context_stack.get()
+
+
+@contextmanager
+def new_context(
+    fresh: bool = False,
+    capture_exceptions: bool = True,
+    client: Optional["Client"] = None,
+):
+    """
+    Create a new context scope that will be active for the duration of the with block.
+    Any tags set within this scope will be isolated to this context. Any exceptions raised
+    or events captured within the context will be tagged with the context tags.
+
+    Args:
+        fresh: Whether to start with a fresh context (default: False).
+               If False, inherits tags, identity and session id's from parent context.
+               If True, starts with no state
+        capture_exceptions: Whether to capture exceptions raised within the context (default: True).
+               If True, captures exceptions and tags them with the context tags before propagating them.
+               If False, exceptions will propagate without being tagged or captured.
+        client: Optional client instance to use for capturing exceptions (default: None).
+                If provided, the client will be used to capture exceptions within the context.
+                If not provided, the default (global) client will be used. Note that the passed
+                client is only used to capture exceptions within the context - other events captured
+                within the context via `Client.capture` or `posthog.capture` will still carry the context
+                state (tags, identity, session id), but will be captured by the client directly used (or
+                the global one, in the case of `posthog.capture`)
+
+    Examples:
+        ```python
+        # Inherit parent context tags
+        with posthog.new_context():
+            posthog.tag("request_id", "123")
+            # Both this event and the exception will be tagged with the context tags
+            posthog.capture("event_name", {"property": "value"})
+            raise ValueError("Something went wrong")
+        ```
+        ```python
+        # Start with fresh context (no inherited tags)
+        with posthog.new_context(fresh=True):
+            posthog.tag("request_id", "123")
+            # Both this event and the exception will be tagged with the context tags
+            posthog.capture("event_name", {"property": "value"})
+            raise ValueError("Something went wrong")
+        ```
+
+    Category:
+        Contexts
+    """
+    from posthog import capture_exception
+
+    current_context = _get_current_context()
+    new_context = ContextScope(current_context, fresh, capture_exceptions, client)
+    _context_stack.set(new_context)
+
+    try:
+        yield
+    except Exception as e:
+        if new_context.capture_exceptions:
+            if new_context.client:
+                new_context.client.capture_exception(e)
+            else:
+                capture_exception(e)
+        raise
+    finally:
+        _context_stack.set(new_context.get_parent())
+
+
+def tag(key: str, value: Any) -> None:
+    """
+    Add a tag to the current context. All tags are added as properties to any event, including exceptions, captured
+    within the context.
+
+    Args:
+        key: The tag key
+        value: The tag value
+
+    Example:
+        ```python
+        posthog.tag("user_id", "123")
+        ```
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.add_tag(key, value)
+
+
+def get_tags() -> Dict[str, Any]:
+    """
+    Get all tags from the current context. Note, modifying
+    the returned dictionary will not affect the current context.
+
+    Returns:
+        Dict of all tags in the current context
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.collect_tags()
+    return {}
+
+
+def identify_context(distinct_id: str) -> None:
+    """
+    Identify the current context with a distinct ID, associating all events captured in this or
+    child contexts with the given distinct ID (unless identify_context is called again). This is overridden by
+    distinct id's passed directly to posthog.capture and related methods (identify, set etc). Entering a
+    fresh context will clear the context-level distinct ID. The distinct-id passed should be uniquely associated
+    with one of your users. Events captured outside of a context, or in a context with no associated distinct
+    ID, will be assigned a random UUID, and captured as "personless".
+
+    Args:
+        distinct_id: The distinct ID to associate with the current context and its children.
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_distinct_id(distinct_id)
+
+
+def set_context_session(session_id: str) -> None:
+    """
+    Set the session ID for the current context, associating all events captured in this or
+    child contexts with the given session ID (unless set_context_session is called again).
+    Entering a fresh context will clear the context-level session ID.
+
+    Args:
+        session_id: The session ID to associate with the current context and its children. See https://posthog.com/docs/data/sessions
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_session_id(session_id)
+
+
+def get_context_session_id() -> Optional[str]:
+    """
+    Get the session ID for the current context.
+
+    Returns:
+        The session ID if set, None otherwise
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_session_id()
+    return None
+
+
+def get_context_distinct_id() -> Optional[str]:
+    """
+    Get the distinct ID for the current context.
+
+    Returns:
+        The distinct ID if set, None otherwise
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_distinct_id()
+    return None
+
+
+def set_context_device_id(device_id: str) -> None:
+    """
+    Set the device ID for the current context, associating all feature flag requests in this or
+    child contexts with the given device ID (unless set_context_device_id is called again).
+    Entering a fresh context will clear the context-level device ID.
+
+    Args:
+        device_id: The device ID to associate with the current context and its children.
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_device_id(device_id)
+
+
+def get_context_device_id() -> Optional[str]:
+    """
+    Get the device ID for the current context.
+
+    Returns:
+        The device ID if set, None otherwise
+
+    Category:
+        Contexts
+    """
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_device_id()
+    return None
+
+
+def set_capture_exception_code_variables_context(enabled: bool) -> None:
+    """
+    Set whether code variables are captured for the current context.
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_capture_exception_code_variables(enabled)
+
+
+def set_code_variables_mask_patterns_context(mask_patterns: list) -> None:
+    """
+    Variable names matching these patterns will be masked with *** when capturing code variables.
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_code_variables_mask_patterns(mask_patterns)
+
+
+def set_code_variables_ignore_patterns_context(ignore_patterns: list) -> None:
+    """
+    Variable names matching these patterns will be ignored completely when capturing code variables.
+    """
+    current_context = _get_current_context()
+    if current_context:
+        current_context.set_code_variables_ignore_patterns(ignore_patterns)
+
+
+def get_capture_exception_code_variables_context() -> Optional[bool]:
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_capture_exception_code_variables()
+    return None
+
+
+def get_code_variables_mask_patterns_context() -> Optional[list]:
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_code_variables_mask_patterns()
+    return None
+
+
+def get_code_variables_ignore_patterns_context() -> Optional[list]:
+    current_context = _get_current_context()
+    if current_context:
+        return current_context.get_code_variables_ignore_patterns()
+    return None
+
+
+F = TypeVar("F", bound=Callable[..., Any])
+
+
+def scoped(fresh: bool = False, capture_exceptions: bool = True):
+    """
+    Decorator that creates a new context for the function. Simply wraps
+    the function in a with posthog.new_context(): block.
+
+    Args:
+        fresh: Whether to start with a fresh context (default: False)
+        capture_exceptions: Whether to capture and track exceptions with posthog error tracking (default: True)
+
+    Example:
+        @posthog.scoped()
+        def process_payment(payment_id):
+            posthog.tag("payment_id", payment_id)
+            posthog.tag("payment_method", "credit_card")
+
+            # This event will be captured with tags
+            posthog.capture("payment_started")
+            # If this raises an exception, it will be captured with tags
+            # and then re-raised
+            some_risky_function()
+
+    Category:
+        Contexts
+    """
+
+    def decorator(func: F) -> F:
+        from functools import wraps
+
+        @wraps(func)
+        def wrapper(*args, **kwargs):
+            with new_context(fresh=fresh, capture_exceptions=capture_exceptions):
+                return func(*args, **kwargs)
+
+        return cast(F, wrapper)
+
+    return decorator

posthog/exception_capture.py

@@ -6,45 +6,25 @@
 import logging
 import sys
 import threading
-from enum import Enum
-from typing import TYPE_CHECKING, List, Optional
+from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
     from posthog.client import Client
 
 
-class Integrations(str, Enum):
-    Django = "django"
-
-
 class ExceptionCapture:
     # TODO: Add client side rate limiting to prevent spamming the server with exceptions
 
     log = logging.getLogger("posthog")
 
-    def __init__(self, client: "Client", integrations: Optional[List[Integrations]] = None):
+    def __init__(self, client: "Client"):
         self.client = client
         self.original_excepthook = sys.excepthook
         sys.excepthook = self.exception_handler
         threading.excepthook = self.thread_exception_handler
-        self.enabled_integrations = []
-
-        for integration in integrations or []:
-            # TODO: Maybe find a better way of enabling integrations
-            # This is very annoying currently if we had to add any configuration per integration
-            if integration == Integrations.Django:
-                try:
-                    from posthog.exception_integrations.django import DjangoIntegration
-
-                    enabled_integration = DjangoIntegration(self.exception_receiver)
-                    self.enabled_integrations.append(enabled_integration)
-                except Exception as e:
-                    self.log.exception(f"Failed to enable Django integration: {e}")
 
     def close(self):
         sys.excepthook = self.original_excepthook
-        for integration in self.enabled_integrations:
-            integration.uninstall()
 
     def exception_handler(self, exc_type, exc_value, exc_traceback):
         # don't affect default behaviour.
@@ -64,6 +44,6 @@ class ExceptionCapture:
     def capture_exception(self, exception, metadata=None):
         try:
             distinct_id = metadata.get("distinct_id") if metadata else None
-            self.client.capture_exception(exception, distinct_id)
+            self.client.capture_exception(exception, distinct_id=distinct_id)
         except Exception as e:
             self.log.exception(f"Failed to capture exception: {e}")

posthog/exception_integrations/__init__.py

@@ -1,5 +0,0 @@
-class IntegrationEnablingError(Exception):
-    """
-    The integration could not be enabled due to a user error like
-    `django` not being installed for the `DjangoIntegration`.
-    """

posthog/exception_integrations/django.py

@@ -1,93 +0,0 @@
-# Portions of this file are derived from getsentry/sentry-javascript by Software, Inc. dba Sentry
-# Licensed under the MIT License
-
-# 💖open source (under MIT License)
-
-import re
-import sys
-from typing import TYPE_CHECKING
-
-from posthog.exception_integrations import IntegrationEnablingError
-
-try:
-    from django import VERSION as DJANGO_VERSION
-    from django.core import signals
-
-except ImportError:
-    raise IntegrationEnablingError("Django not installed")
-
-
-if TYPE_CHECKING:
-    from typing import Any, Dict  # noqa: F401
-
-    from django.core.handlers.wsgi import WSGIRequest  # noqa: F401
-
-
-class DjangoIntegration:
-    # TODO: Abstract integrations one we have more and can see patterns
-    """
-    Autocapture errors from a Django application.
-    """
-
-    identifier = "django"
-
-    def __init__(self, capture_exception_fn=None):
-
-        if DJANGO_VERSION < (4, 2):
-            raise IntegrationEnablingError("Django 4.2 or newer is required.")
-
-        # TODO: Right now this seems too complicated / overkill for us, but seems like we can automatically plug in middlewares
-        # which is great for users (they don't need to do this) and everything should just work.
-        # We should consider this in the future, but for now we can just use the middleware and signals handlers.
-        # See: https://github.com/getsentry/sentry-python/blob/269d96d6e9821122fbff280e6a26956e5ed03c0b/sentry_sdk/integrations/django/__init__.py
-
-        self.capture_exception_fn = capture_exception_fn
-
-        def _got_request_exception(request=None, **kwargs):
-            # type: (WSGIRequest, **Any) -> None
-
-            extra_props = {}
-            if request is not None:
-                # get headers metadata
-                extra_props = DjangoRequestExtractor(request).extract_person_data()
-
-            self.capture_exception_fn(sys.exc_info(), extra_props)
-
-        signals.got_request_exception.connect(_got_request_exception)
-
-    def uninstall(self):
-        pass
-
-
-class DjangoRequestExtractor:
-
-    def __init__(self, request):
-        # type: (Any) -> None
-        self.request = request
-
-    def extract_person_data(self):
-        headers = self.headers()
-
-        # Extract traceparent and tracestate headers
-        traceparent = headers.get("traceparent")
-        tracestate = headers.get("tracestate")
-
-        # Extract the distinct_id from tracestate
-        distinct_id = None
-        if tracestate:
-            # TODO: Align on the format of the distinct_id in tracestate
-            # We can't have comma or equals in header values here, so maybe we should base64 encode it?
-            match = re.search(r"posthog-distinct-id=([^,]+)", tracestate)
-            if match:
-                distinct_id = match.group(1)
-
-        return {
-            "distinct_id": distinct_id,
-            "ip": headers.get("X-Forwarded-For"),
-            "user_agent": headers.get("User-Agent"),
-            "traceparent": traceparent,
-        }
-
-    def headers(self):
-        # type: () -> Dict[str, str]
-        return dict(self.request.headers)

posthog/exception_utils.py

@@ -5,12 +5,32 @@
 # 💖open source (under MIT License)
 # We want to keep payloads as similar to Sentry as possible for easy interoperability
 
+import json
 import linecache
 import os
 import re
 import sys
+import types
 from datetime import datetime
-from typing import TYPE_CHECKING
+from types import FrameType, TracebackType  # noqa: F401
+from typing import (  # noqa: F401
+    TYPE_CHECKING,
+    Any,
+    Dict,
+    Iterator,
+    List,
+    Literal,
+    Optional,
+    Pattern,
+    Set,
+    Tuple,
+    TypedDict,
+    TypeVar,
+    Union,
+    cast,
+)
+
+from posthog.args import ExceptionArg, ExcInfo  # noqa: F401
 
 try:
     # Python 3.11
@@ -22,78 +42,101 @@ except ImportError:
 
 DEFAULT_MAX_VALUE_LENGTH = 1024
 
+DEFAULT_CODE_VARIABLES_MASK_PATTERNS = [
+    r"(?i).*password.*",
+    r"(?i).*secret.*",
+    r"(?i).*passwd.*",
+    r"(?i).*pwd.*",
+    r"(?i).*api_key.*",
+    r"(?i).*apikey.*",
+    r"(?i).*auth.*",
+    r"(?i).*credentials.*",
+    r"(?i).*privatekey.*",
+    r"(?i).*private_key.*",
+    r"(?i).*token.*",
+    r"(?i).*aws_access_key_id.*",
+    r"(?i).*_pass",
+    r"(?i)sk_.*",
+    r"(?i).*jwt.*",
+]
 
-if TYPE_CHECKING:
+DEFAULT_CODE_VARIABLES_IGNORE_PATTERNS = [r"^__.*"]
 
-    from types import FrameType, TracebackType
-    from typing import (  # noqa: F401
-        Any,
-        Callable,
-        Dict,
-        Iterator,
-        List,
-        Literal,
-        Optional,
-        Set,
-        Tuple,
-        Type,
-        TypedDict,
-        TypeVar,
-        Union,
-        cast,
-    )
+CODE_VARIABLES_REDACTED_VALUE = "$$_posthog_redacted_based_on_masking_rules_$$"
 
-    ExcInfo = Union[
-        Tuple[Type[BaseException], BaseException, Optional[TracebackType]],
-        Tuple[None, None, None],
-    ]
-    LogLevelStr = Literal["fatal", "critical", "error", "warning", "info", "debug"]
+DEFAULT_TOTAL_VARIABLES_SIZE_LIMIT = 20 * 1024
 
-    Event = TypedDict(
-        "Event",
-        {
-            "breadcrumbs": Dict[Literal["values"], List[Dict[str, Any]]],  # TODO: We can expand on this type
-            "check_in_id": str,
-            "contexts": Dict[str, Dict[str, object]],
-            "dist": str,
-            "duration": Optional[float],
-            "environment": str,
-            "errors": List[Dict[str, Any]],  # TODO: We can expand on this type
-            "event_id": str,
-            "exception": Dict[Literal["values"], List[Dict[str, Any]]],  # TODO: We can expand on this type
-            # "extra": MutableMapping[str, object],
-            # "fingerprint": List[str],
-            "level": LogLevelStr,
-            # "logentry": Mapping[str, object],
-            "logger": str,
-            # "measurements": Dict[str, MeasurementValue],
-            "message": str,
-            "modules": Dict[str, str],
-            # "monitor_config": Mapping[str, object],
-            "monitor_slug": Optional[str],
-            "platform": Literal["python"],
-            "profile": object,  # Should be sentry_sdk.profiler.Profile, but we can't import that here due to circular imports
-            "release": str,
-            "request": Dict[str, object],
-            # "sdk": Mapping[str, object],
-            "server_name": str,
-            "spans": List[Dict[str, object]],
-            "stacktrace": Dict[str, object],  # We access this key in the code, but I am unsure whether we ever set it
-            "start_timestamp": datetime,
-            "status": Optional[str],
-            # "tags": MutableMapping[
-            #     str, str
-            # ],  # Tags must be less than 200 characters each
-            "threads": Dict[Literal["values"], List[Dict[str, Any]]],  # TODO: We can expand on this type
-            "timestamp": Optional[datetime],  # Must be set before sending the event
-            "transaction": str,
-            # "transaction_info": Mapping[str, Any],  # TODO: We can expand on this type
-            "type": Literal["check_in", "transaction"],
-            "user": Dict[str, object],
-            "_metrics_summary": Dict[str, object],
-        },
-        total=False,
-    )
+
+class VariableSizeLimiter:
+    def __init__(self, max_size=DEFAULT_TOTAL_VARIABLES_SIZE_LIMIT):
+        self.max_size = max_size
+        self.current_size = 0
+
+    def can_add(self, size):
+        return self.current_size + size <= self.max_size
+
+    def add(self, size):
+        self.current_size += size
+
+    def get_remaining_space(self):
+        return self.max_size - self.current_size
+
+
+LogLevelStr = Literal["fatal", "critical", "error", "warning", "info", "debug"]
+
+Event = TypedDict(
+    "Event",
+    {
+        "breadcrumbs": Dict[
+            Literal["values"], List[Dict[str, Any]]
+        ],  # TODO: We can expand on this type
+        "check_in_id": str,
+        "contexts": Dict[str, Dict[str, object]],
+        "dist": str,
+        "duration": Optional[float],
+        "environment": str,
+        "errors": List[Dict[str, Any]],  # TODO: We can expand on this type
+        "event_id": str,
+        "exception": Dict[
+            Literal["values"], List[Dict[str, Any]]
+        ],  # TODO: We can expand on this type
+        # "extra": MutableMapping[str, object],
+        # "fingerprint": List[str],
+        "level": LogLevelStr,
+        # "logentry": Mapping[str, object],
+        "logger": str,
+        # "measurements": Dict[str, MeasurementValue],
+        "message": str,
+        "modules": Dict[str, str],
+        # "monitor_config": Mapping[str, object],
+        "monitor_slug": Optional[str],
+        "platform": Literal["python"],
+        "profile": object,
+        "release": str,
+        "request": Dict[str, object],
+        # "sdk": Mapping[str, object],
+        "server_name": str,
+        "spans": List[Dict[str, object]],
+        "stacktrace": Dict[
+            str, object
+        ],  # We access this key in the code, but I am unsure whether we ever set it
+        "start_timestamp": datetime,
+        "status": Optional[str],
+        # "tags": MutableMapping[
+        #     str, str
+        # ],  # Tags must be less than 200 characters each
+        "threads": Dict[
+            Literal["values"], List[Dict[str, Any]]
+        ],  # TODO: We can expand on this type
+        "timestamp": Optional[datetime],  # Must be set before sending the event
+        "transaction": str,
+        # "transaction_info": Mapping[str, Any],  # TODO: We can expand on this type
+        "type": Literal["check_in", "transaction"],
+        "user": Dict[str, object],
+        "_metrics_summary": Dict[str, object],
+    },
+    total=False,
+)
 
 
 epoch = datetime(1970, 1, 1)
@@ -129,9 +172,6 @@ def event_hint_with_exc_info(exc_info=None):
 class AnnotatedValue:
     """
     Meta information for a data field in the event payload.
-    This is to tell Relay that we have tampered with the fields value.
-    See:
-    https://github.com/getsentry/relay/blob/be12cd49a0f06ea932ed9b9f93a655de5d6ad6d1/relay-general/src/types/meta.rs#L407-L423
     """
 
     __slots__ = ("value", "metadata")
@@ -273,7 +313,10 @@ def get_lines_from_file(
     upper_bound = min(lineno + 1 + context_lines, len(source))
 
     try:
-        pre_context = [strip_string(line.strip("\r\n"), max_length=max_length) for line in source[lower_bound:lineno]]
+        pre_context = [
+            strip_string(line.strip("\r\n"), max_length=max_length)
+            for line in source[lower_bound:lineno]
+        ]
         context_line = strip_string(source[lineno].strip("\r\n"), max_length=max_length)
         post_context = [
             strip_string(line.strip("\r\n"), max_length=max_length)
@@ -305,7 +348,9 @@ def get_source_context(
         loader = None
     lineno = tb_lineno - 1
     if lineno is not None and abs_path:
-        return get_lines_from_file(abs_path, lineno, max_value_length, loader=loader, module=module)
+        return get_lines_from_file(
+            abs_path, lineno, max_value_length, loader=loader, module=module
+        )
     return [], None, []
 
 
@@ -342,7 +387,9 @@ def filename_for_module(module, abs_path):
         if not base_module_path:
             return abs_path
 
-        return abs_path.split(base_module_path.rsplit(os.sep, 2)[0], 1)[-1].lstrip(os.sep)
+        return abs_path.split(base_module_path.rsplit(os.sep, 2)[0], 1)[-1].lstrip(
+            os.sep
+        )
     except Exception:
         return abs_path
 
@@ -350,12 +397,9 @@ def filename_for_module(module, abs_path):
 def serialize_frame(
     frame,
     tb_lineno=None,
-    include_local_variables=True,
-    include_source_context=True,
     max_value_length=None,
-    custom_repr=None,
 ):
-    # type: (FrameType, Optional[int], bool, bool, Optional[int], Optional[Callable[..., Optional[str]]]) -> Dict[str, Any]
+    # type: (FrameType, Optional[int], Optional[int]) -> Dict[str, Any]
     f_code = getattr(frame, "f_code", None)
     if not f_code:
         abs_path = None
@@ -380,50 +424,13 @@ def serialize_frame(
         "lineno": tb_lineno,
     }  # type: Dict[str, Any]
 
-    if include_source_context:
-        rv["pre_context"], rv["context_line"], rv["post_context"] = get_source_context(
-            frame, tb_lineno, max_value_length
-        )
-
-    if include_local_variables:
-        # TODO(nk): Sort out this current invalid import
-        # from sentry_sdk.serializer import serialize
-
-        # rv["vars"] = serialize(
-        #     dict(frame.f_locals), is_vars=True, custom_repr=custom_repr
-        # )
-        pass
+    rv["pre_context"], rv["context_line"], rv["post_context"] = get_source_context(
+        frame, tb_lineno, max_value_length
+    )
 
     return rv
 
 
-def current_stacktrace(
-    include_local_variables=True,  # type: bool
-    include_source_context=True,  # type: bool
-    max_value_length=None,  # type: Optional[int]
-):
-    # type: (...) -> Dict[str, Any]
-    __tracebackhide__ = True
-    frames = []
-
-    f = sys._getframe()  # type: Optional[FrameType]
-    while f is not None:
-        if not should_hide_frame(f):
-            frames.append(
-                serialize_frame(
-                    f,
-                    include_local_variables=include_local_variables,
-                    include_source_context=include_source_context,
-                    max_value_length=max_value_length,
-                )
-            )
-        f = f.f_back
-
-    frames.reverse()
-
-    return {"frames": frames, "type": "raw"}
-
-
 def get_errno(exc_value):
     # type: (BaseException) -> Optional[Any]
     return getattr(exc_value, "errno", None)
@@ -431,14 +438,19 @@ def get_errno(exc_value):
 
 def get_error_message(exc_value):
     # type: (Optional[BaseException]) -> str
-    return getattr(exc_value, "message", "") or getattr(exc_value, "detail", "") or safe_str(exc_value)
+    message = (
+        getattr(exc_value, "message", "")
+        or getattr(exc_value, "detail", "")
+        or exc_value
+    )
+
+    return safe_str(message)
 
 
 def single_exception_from_error_tuple(
     exc_type,  # type: Optional[type]
     exc_value,  # type: Optional[BaseException]
     tb,  # type: Optional[TracebackType]
-    client_options=None,  # type: Optional[Dict[str, Any]]
     mechanism=None,  # type: Optional[Dict[str, Any]]
     exception_id=None,  # type: Optional[int]
     parent_id=None,  # type: Optional[int]
@@ -446,13 +458,12 @@ def single_exception_from_error_tuple(
 ):
     # type: (...) -> Dict[str, Any]
     """
-    Creates a dict that goes into the events `exception.values` list and is ingestible by Sentry.
-
-    See the Exception Interface documentation for more details:
-    https://develop.sentry.dev/sdk/event-payloads/exception/
+    Creates a dict that goes into the events `exception.values` list
     """
     exception_value = {}  # type: Dict[str, Any]
-    exception_value["mechanism"] = mechanism.copy() if mechanism else {"type": "generic", "handled": True}
+    exception_value["mechanism"] = (
+        mechanism.copy() if mechanism else {"type": "generic", "handled": True}
+    )
     if exception_id is not None:
         exception_value["mechanism"]["exception_id"] = exception_id
 
@@ -462,7 +473,9 @@ def single_exception_from_error_tuple(
         errno = None
 
     if errno is not None:
-        exception_value["mechanism"].setdefault("meta", {}).setdefault("errno", {}).setdefault("number", errno)
+        exception_value["mechanism"].setdefault("meta", {}).setdefault(
+            "errno", {}
+        ).setdefault("number", errno)
 
     if source is not None:
         exception_value["mechanism"]["source"] = source
@@ -475,7 +488,9 @@ def single_exception_from_error_tuple(
     if is_root_exception and "type" not in exception_value["mechanism"]:
         exception_value["mechanism"]["type"] = "generic"
 
-    is_exception_group = BaseExceptionGroup is not None and isinstance(exc_value, BaseExceptionGroup)
+    is_exception_group = BaseExceptionGroup is not None and isinstance(
+        exc_value, BaseExceptionGroup
+    )
     if is_exception_group:
         exception_value["mechanism"]["is_exception_group"] = True
 
@@ -483,25 +498,13 @@ def single_exception_from_error_tuple(
     exception_value["type"] = get_type_name(exc_type)
     exception_value["value"] = get_error_message(exc_value)
 
-    if client_options is None:
-        include_local_variables = True
-        include_source_context = True
-        max_value_length = DEFAULT_MAX_VALUE_LENGTH  # fallback
-        custom_repr = None
-    else:
-        include_local_variables = client_options["include_local_variables"]
-        include_source_context = client_options["include_source_context"]
-        max_value_length = client_options["max_value_length"]
-        custom_repr = client_options.get("custom_repr")
+    max_value_length = DEFAULT_MAX_VALUE_LENGTH  # fallback
 
     frames = [
         serialize_frame(
             tb.tb_frame,
             tb_lineno=tb.tb_lineno,
-            include_local_variables=include_local_variables,
-            include_source_context=include_source_context,
             max_value_length=max_value_length,
-            custom_repr=custom_repr,
         )
         for tb in iter_stacks(tb)
     ]
@@ -523,7 +526,11 @@ if HAS_CHAINED_EXCEPTIONS:
         seen_exceptions = []
         seen_exception_ids = set()  # type: Set[int]
 
-        while exc_type is not None and exc_value is not None and id(exc_value) not in seen_exception_ids:
+        while (
+            exc_type is not None
+            and exc_value is not None
+            and id(exc_value) not in seen_exception_ids
+        ):
             yield exc_type, exc_value, tb
 
             # Avoid hashing random types we don't know anything
@@ -553,7 +560,6 @@ def exceptions_from_error(
     exc_type,  # type: Optional[type]
     exc_value,  # type: Optional[BaseException]
     tb,  # type: Optional[TracebackType]
-    client_options=None,  # type: Optional[Dict[str, Any]]
     mechanism=None,  # type: Optional[Dict[str, Any]]
     exception_id=0,  # type: int
     parent_id=0,  # type: int
@@ -563,16 +569,12 @@ def exceptions_from_error(
     """
     Creates the list of exceptions.
     This can include chained exceptions and exceptions from an ExceptionGroup.
-
-    See the Exception Interface documentation for more details:
-    https://develop.sentry.dev/sdk/event-payloads/exception/
     """
 
     parent = single_exception_from_error_tuple(
         exc_type=exc_type,
         exc_value=exc_value,
         tb=tb,
-        client_options=client_options,
         mechanism=mechanism,
         exception_id=exception_id,
         parent_id=parent_id,
@@ -583,18 +585,23 @@ def exceptions_from_error(
     parent_id = exception_id
     exception_id += 1
 
-    should_supress_context = hasattr(exc_value, "__suppress_context__") and exc_value.__suppress_context__  # type: ignore
+    should_supress_context = (
+        hasattr(exc_value, "__suppress_context__") and exc_value.__suppress_context__  # type: ignore
+    )
     if should_supress_context:
         # Add direct cause.
         # The field `__cause__` is set when raised with the exception (using the `from` keyword).
-        exception_has_cause = exc_value and hasattr(exc_value, "__cause__") and exc_value.__cause__ is not None
+        exception_has_cause = (
+            exc_value
+            and hasattr(exc_value, "__cause__")
+            and exc_value.__cause__ is not None
+        )
         if exception_has_cause:
             cause = exc_value.__cause__  # type: ignore
             (exception_id, child_exceptions) = exceptions_from_error(
                 exc_type=type(cause),
                 exc_value=cause,
                 tb=getattr(cause, "__traceback__", None),
-                client_options=client_options,
                 mechanism=mechanism,
                 exception_id=exception_id,
                 source="__cause__",
@@ -604,14 +611,17 @@ def exceptions_from_error(
     else:
         # Add indirect cause.
         # The field `__context__` is assigned if another exception occurs while handling the exception.
-        exception_has_content = exc_value and hasattr(exc_value, "__context__") and exc_value.__context__ is not None
+        exception_has_content = (
+            exc_value
+            and hasattr(exc_value, "__context__")
+            and exc_value.__context__ is not None
+        )
         if exception_has_content:
             context = exc_value.__context__  # type: ignore
             (exception_id, child_exceptions) = exceptions_from_error(
                 exc_type=type(context),
                 exc_value=context,
                 tb=getattr(context, "__traceback__", None),
-                client_options=client_options,
                 mechanism=mechanism,
                 exception_id=exception_id,
                 source="__context__",
@@ -626,7 +636,6 @@ def exceptions_from_error(
                 exc_type=type(e),
                 exc_value=e,
                 tb=getattr(e, "__traceback__", None),
-                client_options=client_options,
                 mechanism=mechanism,
                 exception_id=exception_id,
                 parent_id=parent_id,
@@ -639,20 +648,20 @@ def exceptions_from_error(
 
 def exceptions_from_error_tuple(
     exc_info,  # type: ExcInfo
-    client_options=None,  # type: Optional[Dict[str, Any]]
     mechanism=None,  # type: Optional[Dict[str, Any]]
 ):
     # type: (...) -> List[Dict[str, Any]]
     exc_type, exc_value, tb = exc_info
 
-    is_exception_group = BaseExceptionGroup is not None and isinstance(exc_value, BaseExceptionGroup)
+    is_exception_group = BaseExceptionGroup is not None and isinstance(
+        exc_value, BaseExceptionGroup
+    )
 
     if is_exception_group:
         (_, exceptions) = exceptions_from_error(
             exc_type=exc_type,
             exc_value=exc_value,
             tb=tb,
-            client_options=client_options,
             mechanism=mechanism,
             exception_id=0,
             parent_id=0,
@@ -661,7 +670,9 @@ def exceptions_from_error_tuple(
     else:
         exceptions = []
         for exc_type, exc_value, tb in walk_exception_chain(exc_info):
-            exceptions.append(single_exception_from_error_tuple(exc_type, exc_value, tb, client_options, mechanism))
+            exceptions.append(
+                single_exception_from_error_tuple(exc_type, exc_value, tb, mechanism)
+            )
 
     exceptions.reverse()
 
@@ -749,11 +760,42 @@ def set_in_app_in_frames(frames, in_app_exclude, in_app_include, project_root=No
     return frames
 
 
+def exception_is_already_captured(error):
+    # type: (ExceptionArg) -> bool
+    if isinstance(error, BaseException):
+        return hasattr(error, "__posthog_exception_captured")
+    # Autocaptured exceptions are passed as a tuple from our system hooks,
+    # the second item is the exception value (the first is the exception type)
+    elif isinstance(error, tuple) and len(error) > 1:
+        return error[1] is not None and hasattr(
+            error[1], "__posthog_exception_captured"
+        )
+    else:
+        return False  # type: ignore[unreachable]
+
+
+def mark_exception_as_captured(error, uuid):
+    # type: (ExceptionArg, str) -> None
+    if isinstance(error, BaseException):
+        setattr(error, "__posthog_exception_captured", True)
+        setattr(error, "__posthog_exception_uuid", uuid)
+    # Autocaptured exceptions are passed as a tuple from our system hooks,
+    # the second item is the exception value (the first is the exception type)
+    elif isinstance(error, tuple) and len(error) > 1:
+        if error[1] is not None:
+            setattr(error[1], "__posthog_exception_captured", True)
+            setattr(error[1], "__posthog_exception_uuid", uuid)
+
+
 def exc_info_from_error(error):
-    # type: (Union[BaseException, ExcInfo]) -> ExcInfo
+    # type: (ExceptionArg) -> ExcInfo
     if isinstance(error, tuple) and len(error) == 3:
         exc_type, exc_value, tb = error
     elif isinstance(error, BaseException):
+        try:
+            construct_artificial_traceback(error)
+        except Exception:
+            pass
         tb = getattr(error, "__traceback__", None)
         if tb is not None:
             exc_type = type(error)
@@ -778,21 +820,29 @@ def exc_info_from_error(error):
     return exc_info
 
 
-def event_from_exception(
-    exc_info,  # type: Union[BaseException, ExcInfo]
-    client_options=None,  # type: Optional[Dict[str, Any]]
-    mechanism=None,  # type: Optional[Dict[str, Any]]
-):
-    # type: (...) -> Tuple[Event, Dict[str, Any]]
-    exc_info = exc_info_from_error(exc_info)
-    hint = event_hint_with_exc_info(exc_info)
-    return (
-        {
-            "level": "error",
-            "exception": {"values": exceptions_from_error_tuple(exc_info, client_options, mechanism)},
-        },
-        hint,
-    )
+def construct_artificial_traceback(e):
+    # type: (BaseException) -> None
+    if getattr(e, "__traceback__", None) is not None:
+        return
+
+    depth = 0
+    frames = []
+    while True:
+        try:
+            frame = sys._getframe(depth)
+            depth += 1
+        except ValueError:
+            break
+
+        frames.append(frame)
+
+    frames.reverse()
+
+    tb = None
+    for frame in frames:
+        tb = types.TracebackType(tb, frame, frame.f_lasti, frame.f_lineno)
+
+    setattr(e, "__traceback__", tb)
 
 
 def _module_in_list(name, items):
@@ -813,7 +863,9 @@ def _module_in_list(name, items):
 def _is_external_source(abs_path):
     # type: (str) -> bool
     # check if frame is in 'site-packages' or 'dist-packages'
-    external_source = re.search(r"[\\/](?:dist|site)-packages[\\/]", abs_path) is not None
+    external_source = (
+        re.search(r"[\\/](?:dist|site)-packages[\\/]", abs_path) is not None
+    )
     return external_source
 
 
@@ -874,3 +926,209 @@ def strip_string(value, max_length=None):
             "rem": [["!limit", "x", max_length - 3, max_length]],
         },
     )
+
+
+def _compile_patterns(patterns):
+    compiled = []
+    for pattern in patterns:
+        try:
+            compiled.append(re.compile(pattern))
+        except Exception:
+            pass
+    return compiled
+
+
+def _pattern_matches(name, patterns):
+    for pattern in patterns:
+        if pattern.search(name):
+            return True
+    return False
+
+
+def _mask_sensitive_data(value, compiled_mask):
+    if not compiled_mask:
+        return value
+
+    if isinstance(value, dict):
+        result = {}
+        for k, v in value.items():
+            key_str = str(k) if not isinstance(k, str) else k
+            if _pattern_matches(key_str, compiled_mask):
+                result[k] = CODE_VARIABLES_REDACTED_VALUE
+            else:
+                result[k] = _mask_sensitive_data(v, compiled_mask)
+        return result
+    elif isinstance(value, (list, tuple)):
+        masked_items = [_mask_sensitive_data(item, compiled_mask) for item in value]
+        return type(value)(masked_items)
+    elif isinstance(value, str):
+        if _pattern_matches(value, compiled_mask):
+            return CODE_VARIABLES_REDACTED_VALUE
+        return value
+    else:
+        return value
+
+
+def _serialize_variable_value(value, limiter, max_length=1024, compiled_mask=None):
+    try:
+        if value is None:
+            result = "None"
+        elif isinstance(value, bool):
+            result = str(value)
+        elif isinstance(value, (int, float)):
+            result_size = len(str(value))
+            if not limiter.can_add(result_size):
+                return None
+            limiter.add(result_size)
+            return value
+        elif isinstance(value, str):
+            if compiled_mask and _pattern_matches(value, compiled_mask):
+                result = CODE_VARIABLES_REDACTED_VALUE
+            else:
+                result = value
+        else:
+            masked_value = _mask_sensitive_data(value, compiled_mask)
+            result = json.dumps(masked_value)
+
+        if len(result) > max_length:
+            result = result[: max_length - 3] + "..."
+
+        result_size = len(result)
+        if not limiter.can_add(result_size):
+            return None
+        limiter.add(result_size)
+
+        return result
+    except Exception:
+        try:
+            result = repr(value)
+            if len(result) > max_length:
+                result = result[: max_length - 3] + "..."
+
+            result_size = len(result)
+            if not limiter.can_add(result_size):
+                return None
+            limiter.add(result_size)
+            return result
+        except Exception:
+            try:
+                fallback = f"<{type(value).__name__}>"
+                fallback_size = len(fallback)
+                if not limiter.can_add(fallback_size):
+                    return None
+                limiter.add(fallback_size)
+                return fallback
+            except Exception:
+                fallback = "<unserializable object>"
+                fallback_size = len(fallback)
+                if not limiter.can_add(fallback_size):
+                    return None
+                limiter.add(fallback_size)
+                return fallback
+
+
+def _is_simple_type(value):
+    return isinstance(value, (type(None), bool, int, float, str))
+
+
+def serialize_code_variables(
+    frame, limiter, mask_patterns=None, ignore_patterns=None, max_length=1024
+):
+    if mask_patterns is None:
+        mask_patterns = []
+    if ignore_patterns is None:
+        ignore_patterns = []
+
+    compiled_mask = _compile_patterns(mask_patterns)
+    compiled_ignore = _compile_patterns(ignore_patterns)
+
+    try:
+        local_vars = frame.f_locals.copy()
+    except Exception:
+        return {}
+
+    simple_vars = {}
+    complex_vars = {}
+
+    for name, value in local_vars.items():
+        if _pattern_matches(name, compiled_ignore):
+            continue
+
+        if _is_simple_type(value):
+            simple_vars[name] = value
+        else:
+            complex_vars[name] = value
+
+    result = {}
+
+    all_vars = {**simple_vars, **complex_vars}
+    ordered_names = list(sorted(simple_vars.keys())) + list(sorted(complex_vars.keys()))
+
+    for name in ordered_names:
+        value = all_vars[name]
+
+        if _pattern_matches(name, compiled_mask):
+            redacted_value = CODE_VARIABLES_REDACTED_VALUE
+            redacted_size = len(redacted_value)
+            if not limiter.can_add(redacted_size):
+                break
+            limiter.add(redacted_size)
+            result[name] = redacted_value
+        else:
+            serialized = _serialize_variable_value(
+                value, limiter, max_length, compiled_mask
+            )
+            if serialized is None:
+                break
+            result[name] = serialized
+
+    return result
+
+
+def try_attach_code_variables_to_frames(
+    all_exceptions, exc_info, mask_patterns, ignore_patterns
+):
+    try:
+        attach_code_variables_to_frames(
+            all_exceptions, exc_info, mask_patterns, ignore_patterns
+        )
+    except Exception:
+        pass
+
+
+def attach_code_variables_to_frames(
+    all_exceptions, exc_info, mask_patterns, ignore_patterns
+):
+    exc_type, exc_value, traceback = exc_info
+
+    if traceback is None:
+        return
+
+    tb_frames = list(iter_stacks(traceback))
+
+    if not tb_frames:
+        return
+
+    limiter = VariableSizeLimiter()
+
+    for exception in all_exceptions:
+        stacktrace = exception.get("stacktrace")
+        if not stacktrace or "frames" not in stacktrace:
+            continue
+
+        serialized_frames = stacktrace["frames"]
+
+        for serialized_frame, tb_item in zip(serialized_frames, tb_frames):
+            if not serialized_frame.get("in_app"):
+                continue
+
+            variables = serialize_code_variables(
+                tb_item.tb_frame,
+                limiter,
+                mask_patterns=mask_patterns,
+                ignore_patterns=ignore_patterns,
+                max_length=1024,
+            )
+
+            if variables:
+                serialized_frame["code_variables"] = variables

posthog/feature_flags.py

@@ -22,6 +22,18 @@ class InconclusiveMatchError(Exception):
     pass
 
 
+class RequiresServerEvaluation(Exception):
+    """
+    Raised when feature flag evaluation requires server-side data that is not
+    available locally (e.g., static cohorts, experience continuity).
+
+    This error should propagate immediately to trigger API fallback, unlike
+    InconclusiveMatchError which allows trying other conditions.
+    """
+
+    pass
+
+
 # This function takes a distinct_id and a feature flag key and returns a float between 0 and 1.
 # Given the same distinct_id and key, it'll always return the same float. These floats are
 # uniformly distributed between 0 and 1, so if we want to show this feature to 20% of traffic
@@ -43,58 +55,251 @@ def get_matching_variant(flag, distinct_id):
 def variant_lookup_table(feature_flag):
     lookup_table = []
     value_min = 0
-    multivariates = ((feature_flag.get("filters") or {}).get("multivariate") or {}).get("variants") or []
+    multivariates = ((feature_flag.get("filters") or {}).get("multivariate") or {}).get(
+        "variants"
+    ) or []
     for variant in multivariates:
         value_max = value_min + variant["rollout_percentage"] / 100
-        lookup_table.append({"value_min": value_min, "value_max": value_max, "key": variant["key"]})
+        lookup_table.append(
+            {"value_min": value_min, "value_max": value_max, "key": variant["key"]}
+        )
         value_min = value_max
     return lookup_table
 
 
-def match_feature_flag_properties(flag, distinct_id, properties, cohort_properties=None) -> FlagValue:
+def evaluate_flag_dependency(
+    property, flags_by_key, evaluation_cache, distinct_id, properties, cohort_properties
+):
+    """
+    Evaluate a flag dependency property according to the dependency chain algorithm.
+
+    Args:
+        property: Flag property with type="flag" and dependency_chain
+        flags_by_key: Dictionary of all flags by their key
+        evaluation_cache: Cache for storing evaluation results
+        distinct_id: The distinct ID being evaluated
+        properties: Person properties for evaluation
+        cohort_properties: Cohort properties for evaluation
+
+    Returns:
+        bool: True if all dependencies in the chain evaluate to True, False otherwise
+    """
+    if flags_by_key is None or evaluation_cache is None:
+        # Cannot evaluate flag dependencies without required context
+        raise InconclusiveMatchError(
+            f"Cannot evaluate flag dependency on '{property.get('key', 'unknown')}' without flags_by_key and evaluation_cache"
+        )
+
+    # Check if dependency_chain is present - it should always be provided for flag dependencies
+    if "dependency_chain" not in property:
+        # Missing dependency_chain indicates malformed server data
+        raise InconclusiveMatchError(
+            f"Flag dependency property for '{property.get('key', 'unknown')}' is missing required 'dependency_chain' field"
+        )
+
+    dependency_chain = property["dependency_chain"]
+
+    # Handle circular dependency (empty chain means circular)
+    if len(dependency_chain) == 0:
+        log.debug(f"Circular dependency detected for flag: {property.get('key')}")
+        raise InconclusiveMatchError(
+            f"Circular dependency detected for flag '{property.get('key', 'unknown')}'"
+        )
+
+    # Evaluate all dependencies in the chain order
+    for dep_flag_key in dependency_chain:
+        if dep_flag_key not in evaluation_cache:
+            # Need to evaluate this dependency first
+            dep_flag = flags_by_key.get(dep_flag_key)
+            if not dep_flag:
+                # Missing flag dependency - cannot evaluate locally
+                evaluation_cache[dep_flag_key] = None
+                raise InconclusiveMatchError(
+                    f"Cannot evaluate flag dependency '{dep_flag_key}' - flag not found in local flags"
+                )
+            else:
+                # Check if the flag is active (same check as in client._compute_flag_locally)
+                if not dep_flag.get("active"):
+                    evaluation_cache[dep_flag_key] = False
+                else:
+                    # Recursively evaluate the dependency
+                    try:
+                        dep_result = match_feature_flag_properties(
+                            dep_flag,
+                            distinct_id,
+                            properties,
+                            cohort_properties,
+                            flags_by_key,
+                            evaluation_cache,
+                        )
+                        evaluation_cache[dep_flag_key] = dep_result
+                    except InconclusiveMatchError as e:
+                        # If we can't evaluate a dependency, store None and propagate the error
+                        evaluation_cache[dep_flag_key] = None
+                        raise InconclusiveMatchError(
+                            f"Cannot evaluate flag dependency '{dep_flag_key}': {e}"
+                        ) from e
+
+        # Check the cached result
+        cached_result = evaluation_cache[dep_flag_key]
+        if cached_result is None:
+            # Previously inconclusive - raise error again
+            raise InconclusiveMatchError(
+                f"Flag dependency '{dep_flag_key}' was previously inconclusive"
+            )
+        elif not cached_result:
+            # Definitive False result - dependency failed
+            return False
+
+    # All dependencies in the chain have been evaluated successfully
+    # Now check if the final flag value matches the expected value in the property
+    flag_key = property.get("key")
+    expected_value = property.get("value")
+    operator = property.get("operator", "exact")
+
+    if flag_key and expected_value is not None:
+        # Get the actual value of the flag we're checking
+        actual_value = evaluation_cache.get(flag_key)
+
+        if actual_value is None:
+            # Flag wasn't evaluated - this shouldn't happen if dependency chain is correct
+            raise InconclusiveMatchError(
+                f"Flag '{flag_key}' was not evaluated despite being in dependency chain"
+            )
+
+        # For flag dependencies, we need to compare the actual flag result with expected value
+        # using the flag_evaluates_to operator logic
+        if operator == "flag_evaluates_to":
+            return matches_dependency_value(expected_value, actual_value)
+        else:
+            # This should never happen, but just to be defensive.
+            raise InconclusiveMatchError(
+                f"Flag dependency property for '{property.get('key', 'unknown')}' has invalid operator '{operator}'"
+            )
+
+    # If no value check needed, return True (all dependencies passed)
+    return True
+
+
+def matches_dependency_value(expected_value, actual_value):
+    """
+    Check if the actual flag value matches the expected dependency value.
+
+    This follows the same logic as the C# MatchesDependencyValue function:
+    - String variant case: check for exact match or boolean true
+    - Boolean case: must match expected boolean value
+
+    Args:
+        expected_value: The expected value from the property
+        actual_value: The actual value returned by the flag evaluation
+
+    Returns:
+        bool: True if the values match according to flag dependency rules
+    """
+    # String variant case - check for exact match or boolean true
+    if isinstance(actual_value, str) and len(actual_value) > 0:
+        if isinstance(expected_value, bool):
+            # Any variant matches boolean true
+            return expected_value
+        elif isinstance(expected_value, str):
+            # variants are case-sensitive, hence our comparison is too
+            return actual_value == expected_value
+        else:
+            return False
+
+    # Boolean case - must match expected boolean value
+    elif isinstance(actual_value, bool) and isinstance(expected_value, bool):
+        return actual_value == expected_value
+
+    # Default case
+    return False
+
+
+def match_feature_flag_properties(
+    flag,
+    distinct_id,
+    properties,
+    cohort_properties=None,
+    flags_by_key=None,
+    evaluation_cache=None,
+) -> FlagValue:
     flag_conditions = (flag.get("filters") or {}).get("groups") or []
     is_inconclusive = False
     cohort_properties = cohort_properties or {}
     # Some filters can be explicitly set to null, which require accessing variants like so
-    flag_variants = ((flag.get("filters") or {}).get("multivariate") or {}).get("variants") or []
+    flag_variants = ((flag.get("filters") or {}).get("multivariate") or {}).get(
+        "variants"
+    ) or []
     valid_variant_keys = [variant["key"] for variant in flag_variants]
 
-    # Stable sort conditions with variant overrides to the top. This ensures that if overrides are present, they are
-    # evaluated first, and the variant override is applied to the first matching condition.
-    sorted_flag_conditions = sorted(
-        flag_conditions,
-        key=lambda condition: 0 if condition.get("variant") else 1,
-    )
-
-    for condition in sorted_flag_conditions:
+    for condition in flag_conditions:
         try:
             # if any one condition resolves to True, we can shortcircuit and return
             # the matching variant
-            if is_condition_match(flag, distinct_id, condition, properties, cohort_properties):
+            if is_condition_match(
+                flag,
+                distinct_id,
+                condition,
+                properties,
+                cohort_properties,
+                flags_by_key,
+                evaluation_cache,
+            ):
                 variant_override = condition.get("variant")
                 if variant_override and variant_override in valid_variant_keys:
                     variant = variant_override
                 else:
                     variant = get_matching_variant(flag, distinct_id)
                 return variant or True
+        except RequiresServerEvaluation:
+            # Static cohort or other missing server-side data - must fallback to API
+            raise
         except InconclusiveMatchError:
+            # Evaluation error (bad regex, invalid date, missing property, etc.)
+            # Track that we had an inconclusive match, but try other conditions
             is_inconclusive = True
 
     if is_inconclusive:
-        raise InconclusiveMatchError("Can't determine if feature flag is enabled or not with given properties")
+        raise InconclusiveMatchError(
+            "Can't determine if feature flag is enabled or not with given properties"
+        )
 
     # We can only return False when either all conditions are False, or
     # no condition was inconclusive.
     return False
 
 
-def is_condition_match(feature_flag, distinct_id, condition, properties, cohort_properties) -> bool:
+def is_condition_match(
+    feature_flag,
+    distinct_id,
+    condition,
+    properties,
+    cohort_properties,
+    flags_by_key=None,
+    evaluation_cache=None,
+) -> bool:
     rollout_percentage = condition.get("rollout_percentage")
     if len(condition.get("properties") or []) > 0:
         for prop in condition.get("properties"):
             property_type = prop.get("type")
             if property_type == "cohort":
-                matches = match_cohort(prop, properties, cohort_properties)
+                matches = match_cohort(
+                    prop,
+                    properties,
+                    cohort_properties,
+                    flags_by_key,
+                    evaluation_cache,
+                    distinct_id,
+                )
+            elif property_type == "flag":
+                matches = evaluate_flag_dependency(
+                    prop,
+                    flags_by_key,
+                    evaluation_cache,
+                    distinct_id,
+                    properties,
+                    cohort_properties,
+                )
             else:
                 matches = match_property(prop, properties)
             if not matches:
@@ -103,7 +308,9 @@ def is_condition_match(feature_flag, distinct_id, condition, properties, cohort_
         if rollout_percentage is None:
             return True
 
-    if rollout_percentage is not None and _hash(feature_flag["key"], distinct_id) > (rollout_percentage / 100):
+    if rollout_percentage is not None and _hash(feature_flag["key"], distinct_id) > (
+        rollout_percentage / 100
+    ):
         return False
 
     return True
@@ -117,7 +324,9 @@ def match_property(property, property_values) -> bool:
     value = property.get("value")
 
     if key not in property_values:
-        raise InconclusiveMatchError("can't match properties without a given property value")
+        raise InconclusiveMatchError(
+            "can't match properties without a given property value"
+        )
 
     if operator == "is_not_set":
         raise InconclusiveMatchError("can't match properties with operator is_not_set")
@@ -131,7 +340,9 @@ def match_property(property, property_values) -> bool:
 
         def compute_exact_match(value, override_value):
             if isinstance(value, list):
-                return str(override_value).casefold() in [str(val).casefold() for val in value]
+                return str(override_value).casefold() in [
+                    str(val).casefold() for val in value
+                ]
             return utils.str_iequals(value, override_value)
 
         if operator == "exact":
@@ -149,10 +360,16 @@ def match_property(property, property_values) -> bool:
         return not utils.str_icontains(override_value, value)
 
     if operator == "regex":
-        return is_valid_regex(str(value)) and re.compile(str(value)).search(str(override_value)) is not None
+        return (
+            is_valid_regex(str(value))
+            and re.compile(str(value)).search(str(override_value)) is not None
+        )
 
     if operator == "not_regex":
-        return is_valid_regex(str(value)) and re.compile(str(value)).search(str(override_value)) is None
+        return (
+            is_valid_regex(str(value))
+            and re.compile(str(value)).search(str(override_value)) is None
+        )
 
     if operator in ("gt", "gte", "lt", "lte"):
         # :TRICKY: We adjust comparison based on the override value passed in,
@@ -191,10 +408,14 @@ def match_property(property, property_values) -> bool:
                 parsed_date = parser.parse(str(value))
                 parsed_date = convert_to_datetime_aware(parsed_date)
         except Exception as e:
-            raise InconclusiveMatchError("The date set on the flag is not a valid format") from e
+            raise InconclusiveMatchError(
+                "The date set on the flag is not a valid format"
+            ) from e
 
         if not parsed_date:
-            raise InconclusiveMatchError("The date set on the flag is not a valid format")
+            raise InconclusiveMatchError(
+                "The date set on the flag is not a valid format"
+            )
 
         if isinstance(override_value, datetime.datetime):
             override_date = convert_to_datetime_aware(override_value)
@@ -218,13 +439,22 @@ def match_property(property, property_values) -> bool:
             except Exception:
                 raise InconclusiveMatchError("The date provided is not a valid format")
         else:
-            raise InconclusiveMatchError("The date provided must be a string or date object")
+            raise InconclusiveMatchError(
+                "The date provided must be a string or date object"
+            )
 
     # if we get here, we don't know how to handle the operator
     raise InconclusiveMatchError(f"Unknown operator {operator}")
 
 
-def match_cohort(property, property_values, cohort_properties) -> bool:
+def match_cohort(
+    property,
+    property_values,
+    cohort_properties,
+    flags_by_key=None,
+    evaluation_cache=None,
+    distinct_id=None,
+) -> bool:
     # Cohort properties are in the form of property groups like this:
     # {
     #     "cohort_id": {
@@ -236,13 +466,29 @@ def match_cohort(property, property_values, cohort_properties) -> bool:
     # }
     cohort_id = str(property.get("value"))
     if cohort_id not in cohort_properties:
-        raise InconclusiveMatchError("can't match cohort without a given cohort property value")
+        raise RequiresServerEvaluation(
+            f"cohort {cohort_id} not found in local cohorts - likely a static cohort that requires server evaluation"
+        )
 
     property_group = cohort_properties[cohort_id]
-    return match_property_group(property_group, property_values, cohort_properties)
+    return match_property_group(
+        property_group,
+        property_values,
+        cohort_properties,
+        flags_by_key,
+        evaluation_cache,
+        distinct_id,
+    )
 
 
-def match_property_group(property_group, property_values, cohort_properties) -> bool:
+def match_property_group(
+    property_group,
+    property_values,
+    cohort_properties,
+    flags_by_key=None,
+    evaluation_cache=None,
+    distinct_id=None,
+) -> bool:
     if not property_group:
         return True
 
@@ -259,7 +505,14 @@ def match_property_group(property_group, property_values, cohort_properties) ->
         # a nested property group
         for prop in properties:
             try:
-                matches = match_property_group(prop, property_values, cohort_properties)
+                matches = match_property_group(
+                    prop,
+                    property_values,
+                    cohort_properties,
+                    flags_by_key,
+                    evaluation_cache,
+                    distinct_id,
+                )
                 if property_group_type == "AND":
                     if not matches:
                         return False
@@ -267,12 +520,17 @@ def match_property_group(property_group, property_values, cohort_properties) ->
                     # OR group
                     if matches:
                         return True
+            except RequiresServerEvaluation:
+                # Immediately propagate - this condition requires server-side data
+                raise
             except InconclusiveMatchError as e:
                 log.debug(f"Failed to compute property {prop} locally: {e}")
                 error_matching_locally = True
 
         if error_matching_locally:
-            raise InconclusiveMatchError("Can't match cohort without a given cohort property value")
+            raise InconclusiveMatchError(
+                "Can't match cohort without a given cohort property value"
+            )
         # if we get here, all matched in AND case, or none matched in OR case
         return property_group_type == "AND"
 
@@ -280,7 +538,23 @@ def match_property_group(property_group, property_values, cohort_properties) ->
         for prop in properties:
             try:
                 if prop.get("type") == "cohort":
-                    matches = match_cohort(prop, property_values, cohort_properties)
+                    matches = match_cohort(
+                        prop,
+                        property_values,
+                        cohort_properties,
+                        flags_by_key,
+                        evaluation_cache,
+                        distinct_id,
+                    )
+                elif prop.get("type") == "flag":
+                    matches = evaluate_flag_dependency(
+                        prop,
+                        flags_by_key,
+                        evaluation_cache,
+                        distinct_id,
+                        property_values,
+                        cohort_properties,
+                    )
                 else:
                     matches = match_property(prop, property_values)
 
@@ -298,18 +572,25 @@ def match_property_group(property_group, property_values, cohort_properties) ->
                         return True
                     if not matches and negation:
                         return True
+            except RequiresServerEvaluation:
+                # Immediately propagate - this condition requires server-side data
+                raise
             except InconclusiveMatchError as e:
                 log.debug(f"Failed to compute property {prop} locally: {e}")
                 error_matching_locally = True
 
         if error_matching_locally:
-            raise InconclusiveMatchError("can't match cohort without a given cohort property value")
+            raise InconclusiveMatchError(
+                "can't match cohort without a given cohort property value"
+            )
 
         # if we get here, all matched in AND case, or none matched in OR case
         return property_group_type == "AND"
 
 
-def relative_date_parse_for_feature_flag_matching(value: str) -> Optional[datetime.datetime]:
+def relative_date_parse_for_feature_flag_matching(
+    value: str,
+) -> Optional[datetime.datetime]:
     regex = r"^-?(?P<number>[0-9]+)(?P<interval>[a-z])$"
     match = re.search(regex, value)
     parsed_dt = datetime.datetime.now(datetime.timezone.utc)

posthog/flag_definition_cache.py

@@ -0,0 +1,127 @@
+"""
+Flag Definition Cache Provider interface for multi-worker environments.
+
+EXPERIMENTAL: This API may change in future minor version bumps.
+
+This module provides an interface for external caching of feature flag definitions,
+enabling multi-worker environments (Kubernetes, load-balanced servers, serverless
+functions) to share flag definitions and reduce API calls.
+
+Usage:
+
+    from posthog import Posthog
+    from posthog.flag_definition_cache import FlagDefinitionCacheProvider
+
+    cache = RedisFlagDefinitionCache(redis_client, "my-team")
+    posthog = Posthog(
+        "<project_api_key>",
+        personal_api_key="<personal_api_key>",
+        flag_definition_cache_provider=cache,
+    )
+"""
+
+from typing import Any, Dict, List, Optional, Protocol, runtime_checkable
+
+from typing_extensions import Required, TypedDict
+
+
+class FlagDefinitionCacheData(TypedDict):
+    """
+    Data structure for cached flag definitions.
+
+    Attributes:
+        flags: List of feature flag definition dictionaries from the API.
+        group_type_mapping: Mapping of group type indices to group names.
+        cohorts: Dictionary of cohort definitions for local evaluation.
+    """
+
+    flags: Required[List[Dict[str, Any]]]
+    group_type_mapping: Required[Dict[str, str]]
+    cohorts: Required[Dict[str, Any]]
+
+
+@runtime_checkable
+class FlagDefinitionCacheProvider(Protocol):
+    """
+    Interface for external caching of feature flag definitions.
+
+    Enables multi-worker environments to share flag definitions, reducing API
+    calls while ensuring all workers have consistent data.
+
+    EXPERIMENTAL: This API may change in future minor version bumps.
+
+    The four methods handle the complete lifecycle of flag definition caching:
+
+    1. `should_fetch_flag_definitions()` - Called before each poll to determine
+       if this worker should fetch new definitions. Use for distributed lock
+       coordination to ensure only one worker fetches at a time.
+
+    2. `get_flag_definitions()` - Called when `should_fetch_flag_definitions()`
+       returns False. Returns cached definitions if available.
+
+    3. `on_flag_definitions_received()` - Called after successfully fetching
+       new definitions from the API. Store the data in your external cache
+       and release any locks.
+
+    4. `shutdown()` - Called when the PostHog client shuts down. Release any
+       distributed locks and clean up resources.
+
+    Error Handling:
+        All methods are wrapped in try/except. Errors will be logged but will
+        never break flag evaluation. On error:
+        - `should_fetch_flag_definitions()` errors default to fetching (fail-safe)
+        - `get_flag_definitions()` errors fall back to API fetch
+        - `on_flag_definitions_received()` errors are logged but flags remain in memory
+        - `shutdown()` errors are logged but shutdown continues
+    """
+
+    def get_flag_definitions(self) -> Optional[FlagDefinitionCacheData]:
+        """
+        Retrieve cached flag definitions.
+
+        Returns:
+            Cached flag definitions if available and valid, None otherwise.
+            Returning None will trigger a fetch from the API if this worker
+            has no flags loaded yet.
+        """
+        ...
+
+    def should_fetch_flag_definitions(self) -> bool:
+        """
+        Determine whether this instance should fetch new flag definitions.
+
+        Use this for distributed lock coordination. Only one worker should
+        return True to avoid thundering herd problems. A typical implementation
+        uses a distributed lock (e.g., Redis SETNX) that expires after the
+        poll interval.
+
+        Returns:
+            True if this instance should fetch from the API, False otherwise.
+            When False, the client will call `get_flag_definitions()` to
+            retrieve cached data instead.
+        """
+        ...
+
+    def on_flag_definitions_received(self, data: FlagDefinitionCacheData) -> None:
+        """
+        Called after successfully receiving new flag definitions from PostHog.
+
+        Use this to store the data in your external cache and release any
+        distributed locks acquired in `should_fetch_flag_definitions()`.
+
+        Args:
+            data: The flag definitions to cache, containing flags,
+                  group_type_mapping, and cohorts.
+        """
+        ...
+
+    def shutdown(self) -> None:
+        """
+        Called when the PostHog client shuts down.
+
+        Use this to release any distributed locks and clean up resources.
+        This method is called even if `should_fetch_flag_definitions()`
+        returned False, so implementations should handle the case where
+        no lock was acquired.
+        """
+        ...

posthog/integrations/django.py

@@ -0,0 +1,319 @@
+from typing import TYPE_CHECKING, cast
+from posthog import contexts
+from posthog.client import Client
+
+try:
+    from asgiref.sync import iscoroutinefunction, markcoroutinefunction
+except ImportError:
+    # Fallback for older Django versions without asgiref
+    import asyncio
+
+    iscoroutinefunction = asyncio.iscoroutinefunction
+
+    # No-op fallback for markcoroutinefunction
+    # Older Django versions without asgiref typically don't support async middleware anyway
+    def markcoroutinefunction(func):
+        return func
+
+
+if TYPE_CHECKING:
+    from django.http import HttpRequest, HttpResponse  # noqa: F401
+    from typing import Callable, Dict, Any, Optional, Union, Awaitable  # noqa: F401
+
+
+class PosthogContextMiddleware:
+    """Middleware to automatically track Django requests.
+
+    This middleware wraps all calls with a posthog context. It attempts to extract the following from the request headers:
+    - Session ID, (extracted from `X-POSTHOG-SESSION-ID`)
+    - Distinct ID, (extracted from `X-POSTHOG-DISTINCT-ID`)
+    - Request URL as $current_url
+    - Request Method as $request_method
+
+    The context will also auto-capture exceptions and send them to PostHog, unless you disable it by setting
+    `POSTHOG_MW_CAPTURE_EXCEPTIONS` to `False` in your Django settings. The exceptions are captured using the
+    global client, unless the setting `POSTHOG_MW_CLIENT` is set to a custom client instance
+
+    The middleware behaviour is customisable through 3 additional functions:
+    - `POSTHOG_MW_EXTRA_TAGS`, which is a Callable[[HttpRequest], Dict[str, Any]] expected to return a dictionary of additional tags to be added to the context.
+    - `POSTHOG_MW_REQUEST_FILTER`, which is a Callable[[HttpRequest], bool] expected to return `False` if the request should not be tracked.
+    - `POSTHOG_MW_TAG_MAP`, which is a Callable[[Dict[str, Any]], Dict[str, Any]], which you can use to modify the tags before they're added to the context.
+
+    You can use the `POSTHOG_MW_TAG_MAP` function to remove any default tags you don't want to capture, or override them with your own values.
+
+    Context tags are automatically included as properties on all events captured within a context, including exceptions.
+    See the context documentation for more information. The extracted distinct ID and session ID, if found, are used to
+    associate all events captured in the middleware context with the same distinct ID and session as currently active on the
+    frontend. See the documentation for `set_context_session` and `identify_context` for more details.
+
+    This middleware is hybrid-capable: it supports both WSGI (sync) and ASGI (async) Django applications. The middleware
+    detects at initialization whether the next middleware in the chain is async or sync, and adapts its behavior accordingly.
+    This ensures compatibility with both pure sync and pure async middleware chains, as well as mixed chains in ASGI mode.
+    """
+
+    sync_capable = True
+    async_capable = True
+
+    def __init__(self, get_response):
+        # type: (Union[Callable[[HttpRequest], HttpResponse], Callable[[HttpRequest], Awaitable[HttpResponse]]]) -> None
+        self.get_response = get_response
+        self._is_coroutine = iscoroutinefunction(get_response)
+
+        # Mark this instance as a coroutine function if get_response is async
+        # This is required for Django to correctly detect async middleware
+        if self._is_coroutine:
+            markcoroutinefunction(self)
+
+        from django.conf import settings
+
+        if hasattr(settings, "POSTHOG_MW_EXTRA_TAGS") and callable(
+            settings.POSTHOG_MW_EXTRA_TAGS
+        ):
+            self.extra_tags = cast(
+                "Optional[Callable[[HttpRequest], Dict[str, Any]]]",
+                settings.POSTHOG_MW_EXTRA_TAGS,
+            )
+        else:
+            self.extra_tags = None
+
+        if hasattr(settings, "POSTHOG_MW_REQUEST_FILTER") and callable(
+            settings.POSTHOG_MW_REQUEST_FILTER
+        ):
+            self.request_filter = cast(
+                "Optional[Callable[[HttpRequest], bool]]",
+                settings.POSTHOG_MW_REQUEST_FILTER,
+            )
+        else:
+            self.request_filter = None
+
+        if hasattr(settings, "POSTHOG_MW_TAG_MAP") and callable(
+            settings.POSTHOG_MW_TAG_MAP
+        ):
+            self.tag_map = cast(
+                "Optional[Callable[[Dict[str, Any]], Dict[str, Any]]]",
+                settings.POSTHOG_MW_TAG_MAP,
+            )
+        else:
+            self.tag_map = None
+
+        if hasattr(settings, "POSTHOG_MW_CAPTURE_EXCEPTIONS") and isinstance(
+            settings.POSTHOG_MW_CAPTURE_EXCEPTIONS, bool
+        ):
+            self.capture_exceptions = settings.POSTHOG_MW_CAPTURE_EXCEPTIONS
+        else:
+            self.capture_exceptions = True
+
+        if hasattr(settings, "POSTHOG_MW_CLIENT") and isinstance(
+            settings.POSTHOG_MW_CLIENT, Client
+        ):
+            self.client = cast("Optional[Client]", settings.POSTHOG_MW_CLIENT)
+        else:
+            self.client = None
+
+    def extract_tags(self, request):
+        # type: (HttpRequest) -> Dict[str, Any]
+        """Extract tags from request in sync context."""
+        user_id, user_email = self.extract_request_user(request)
+        return self._build_tags(request, user_id, user_email)
+
+    def _build_tags(self, request, user_id, user_email):
+        # type: (HttpRequest, Optional[str], Optional[str]) -> Dict[str, Any]
+        """
+        Build tags dict from request and user info.
+
+        Centralized tag extraction logic used by both sync and async paths.
+        """
+        tags = {}
+
+        # Extract session ID from X-POSTHOG-SESSION-ID header
+        session_id = request.headers.get("X-POSTHOG-SESSION-ID")
+        if session_id:
+            contexts.set_context_session(session_id)
+
+        # Extract distinct ID from X-POSTHOG-DISTINCT-ID header or request user id
+        distinct_id = request.headers.get("X-POSTHOG-DISTINCT-ID") or user_id
+        if distinct_id:
+            contexts.identify_context(distinct_id)
+
+        # Extract user email
+        if user_email:
+            tags["email"] = user_email
+
+        # Extract current URL
+        absolute_url = request.build_absolute_uri()
+        if absolute_url:
+            tags["$current_url"] = absolute_url
+
+        # Extract request method
+        if request.method:
+            tags["$request_method"] = request.method
+
+        # Extract request path
+        if request.path:
+            tags["$request_path"] = request.path
+
+        # Extract IP address
+        ip_address = request.headers.get("X-Forwarded-For")
+        if ip_address:
+            tags["$ip_address"] = ip_address
+
+        # Extract user agent
+        user_agent = request.headers.get("User-Agent")
+        if user_agent:
+            tags["$user_agent"] = user_agent
+
+        # Apply extra tags if configured
+        if self.extra_tags:
+            extra = self.extra_tags(request)
+            if extra:
+                tags.update(extra)
+
+        # Apply tag mapping if configured
+        if self.tag_map:
+            tags = self.tag_map(tags)
+
+        return tags
+
+    def extract_request_user(self, request):
+        # type: (HttpRequest) -> tuple[Optional[str], Optional[str]]
+        """Extract user ID and email from request in sync context."""
+        user = getattr(request, "user", None)
+        return self._resolve_user_details(user)
+
+    async def aextract_tags(self, request):
+        # type: (HttpRequest) -> Dict[str, Any]
+        """
+        Async version of extract_tags for use in async request handling.
+
+        Uses await request.auser() instead of request.user to avoid
+        SynchronousOnlyOperation in async context.
+
+        Follows Django's naming convention for async methods (auser, asave, etc.).
+        """
+        user_id, user_email = await self.aextract_request_user(request)
+        return self._build_tags(request, user_id, user_email)
+
+    async def aextract_request_user(self, request):
+        # type: (HttpRequest) -> tuple[Optional[str], Optional[str]]
+        """
+        Async version of extract_request_user for use in async request handling.
+
+        Uses await request.auser() instead of request.user to avoid
+        SynchronousOnlyOperation in async context.
+
+        Follows Django's naming convention for async methods (auser, asave, etc.).
+        """
+        auser = getattr(request, "auser", None)
+        if callable(auser):
+            try:
+                user = await auser()
+                return self._resolve_user_details(user)
+            except Exception:
+                # If auser() fails, return empty - don't break the request
+                # Real errors (permissions, broken auth) will be logged by Django
+                return None, None
+
+        # Fallback for test requests without auser
+        return None, None
+
+    def _resolve_user_details(self, user):
+        # type: (Any) -> tuple[Optional[str], Optional[str]]
+        """
+        Extract user ID and email from a user object.
+
+        Handles both authenticated and unauthenticated users, as well as
+        legacy Django where is_authenticated was a method.
+        """
+        user_id = None
+        email = None
+
+        if user is None:
+            return user_id, email
+
+        # Handle is_authenticated (property in modern Django, method in legacy)
+        is_authenticated = getattr(user, "is_authenticated", False)
+        if callable(is_authenticated):
+            is_authenticated = is_authenticated()
+
+        if not is_authenticated:
+            return user_id, email
+
+        # Extract user primary key
+        user_pk = getattr(user, "pk", None)
+        if user_pk is not None:
+            user_id = str(user_pk)
+
+        # Extract user email
+        user_email = getattr(user, "email", None)
+        if user_email:
+            email = str(user_email)
+
+        return user_id, email
+
+    def __call__(self, request):
+        # type: (HttpRequest) -> Union[HttpResponse, Awaitable[HttpResponse]]
+        """
+        Unified entry point for both sync and async request handling.
+
+        When sync_capable and async_capable are both True, Django passes requests
+        without conversion. This method detects the mode and routes accordingly.
+        """
+        if self._is_coroutine:
+            return self.__acall__(request)
+        else:
+            # Synchronous path
+            if self.request_filter and not self.request_filter(request):
+                return self.get_response(request)
+
+            with contexts.new_context(self.capture_exceptions, client=self.client):
+                for k, v in self.extract_tags(request).items():
+                    contexts.tag(k, v)
+
+                return self.get_response(request)
+
+    async def __acall__(self, request):
+        # type: (HttpRequest) -> Awaitable[HttpResponse]
+        """
+        Asynchronous entry point for async request handling.
+
+        This method is called when the middleware chain is async.
+        Uses aextract_tags() which calls request.auser() to avoid
+        SynchronousOnlyOperation when accessing user in async context.
+        """
+        if self.request_filter and not self.request_filter(request):
+            return await self.get_response(request)
+
+        with contexts.new_context(self.capture_exceptions, client=self.client):
+            for k, v in (await self.aextract_tags(request)).items():
+                contexts.tag(k, v)
+
+            return await self.get_response(request)
+
+    def process_exception(self, request, exception):
+        # type: (HttpRequest, Exception) -> None
+        """
+        Process exceptions from views and downstream middleware.
+
+        Django calls this WHILE still inside the context created by __call__,
+        so request tags have already been extracted and set. This method just
+        needs to capture the exception directly.
+
+        Django converts view exceptions into responses before they propagate through
+        the middleware stack, so the context manager in __call__/__acall__ never sees them.
+
+        Note: Django's process_exception is always synchronous, even for async views.
+        """
+        if self.request_filter and not self.request_filter(request):
+            return
+
+        if not self.capture_exceptions:
+            return
+
+        # Context and tags already set by __call__ or __acall__
+        # Just capture the exception
+        if self.client:
+            self.client.capture_exception(exception)
+        else:
+            from posthog import capture_exception
+
+            capture_exception(exception)

posthog/request.py

@@ -1,28 +1,163 @@
 import json
 import logging
+import re
+import socket
+from dataclasses import dataclass
 from datetime import date, datetime
 from gzip import GzipFile
 from io import BytesIO
-from typing import Any, Optional, Union
+from typing import Any, List, Optional, Tuple, Union
 
 import requests
 from dateutil.tz import tzutc
+from requests.adapters import HTTPAdapter  # type: ignore[import-untyped]
+from urllib3.connection import HTTPConnection
 from urllib3.util.retry import Retry
 
 from posthog.utils import remove_trailing_slash
 from posthog.version import VERSION
 
-# Retry on both connect and read errors
-# by default read errors will only retry idempotent HTTP methods (so not POST)
-adapter = requests.adapters.HTTPAdapter(
-    max_retries=Retry(
-        total=2,
-        connect=2,
-        read=2,
+SocketOptions = List[Tuple[int, int, Union[int, bytes]]]
+
+KEEPALIVE_IDLE_SECONDS = 60
+KEEPALIVE_INTERVAL_SECONDS = 60
+KEEPALIVE_PROBE_COUNT = 3
+
+# TCP keepalive probes idle connections to prevent them from being dropped.
+# SO_KEEPALIVE is cross-platform, but timing options vary:
+# - Linux: TCP_KEEPIDLE, TCP_KEEPINTVL, TCP_KEEPCNT
+# - macOS: only SO_KEEPALIVE (uses system defaults)
+# - Windows: TCP_KEEPIDLE, TCP_KEEPINTVL (since Windows 10 1709)
+KEEP_ALIVE_SOCKET_OPTIONS: SocketOptions = list(
+    HTTPConnection.default_socket_options
+) + [
+    (socket.SOL_SOCKET, socket.SO_KEEPALIVE, 1),
+]
+for attr, value in [
+    ("TCP_KEEPIDLE", KEEPALIVE_IDLE_SECONDS),
+    ("TCP_KEEPINTVL", KEEPALIVE_INTERVAL_SECONDS),
+    ("TCP_KEEPCNT", KEEPALIVE_PROBE_COUNT),
+]:
+    if hasattr(socket, attr):
+        KEEP_ALIVE_SOCKET_OPTIONS.append((socket.SOL_TCP, getattr(socket, attr), value))
+
+# Status codes that indicate transient server errors worth retrying
+RETRY_STATUS_FORCELIST = [408, 500, 502, 503, 504]
+
+
+def _mask_tokens_in_url(url: str) -> str:
+    """Mask token values in URLs for safe logging, keeping first 10 chars visible."""
+    return re.sub(r"(token=)([^&]{10})[^&]*", r"\1\2...", url)
+
+
+@dataclass
+class GetResponse:
+    """Response from a GET request with ETag support."""
+
+    data: Any
+    etag: Optional[str] = None
+    not_modified: bool = False
+
+
+class HTTPAdapterWithSocketOptions(HTTPAdapter):
+    """HTTPAdapter with configurable socket options."""
+
+    def __init__(self, *args, socket_options: Optional[SocketOptions] = None, **kwargs):
+        self.socket_options = socket_options
+        super().__init__(*args, **kwargs)
+
+    def init_poolmanager(self, *args, **kwargs):
+        if self.socket_options is not None:
+            kwargs["socket_options"] = self.socket_options
+        super().init_poolmanager(*args, **kwargs)
+
+
+def _build_session(socket_options: Optional[SocketOptions] = None) -> requests.Session:
+    """Build a session for general requests (batch, decide, etc.)."""
+    adapter = HTTPAdapterWithSocketOptions(
+        max_retries=Retry(
+            total=2,
+            connect=2,
+            read=2,
+        ),
+        socket_options=socket_options,
     )
-)
-_session = requests.sessions.Session()
-_session.mount("https://", adapter)
+    session = requests.Session()
+    session.mount("https://", adapter)
+    return session
+
+
+def _build_flags_session(
+    socket_options: Optional[SocketOptions] = None,
+) -> requests.Session:
+    """
+    Build a session for feature flag requests with POST retries.
+
+    Feature flag requests are idempotent (read-only), so retrying POST
+    requests is safe. This session retries on transient server errors
+    (408, 5xx) and network failures with exponential backoff
+    (0.5s, 1s delays between retries).
+    """
+    adapter = HTTPAdapterWithSocketOptions(
+        max_retries=Retry(
+            total=2,
+            connect=2,
+            read=2,
+            backoff_factor=0.5,
+            status_forcelist=RETRY_STATUS_FORCELIST,
+            allowed_methods=["POST"],
+        ),
+        socket_options=socket_options,
+    )
+    session = requests.Session()
+    session.mount("https://", adapter)
+    return session
+
+
+_session = _build_session()
+_flags_session = _build_flags_session()
+_socket_options: Optional[SocketOptions] = None
+_pooling_enabled = True
+
+
+def _get_session() -> requests.Session:
+    if _pooling_enabled:
+        return _session
+    return _build_session(_socket_options)
+
+
+def _get_flags_session() -> requests.Session:
+    if _pooling_enabled:
+        return _flags_session
+    return _build_flags_session(_socket_options)
+
+
+def set_socket_options(socket_options: Optional[SocketOptions]) -> None:
+    """
+    Configure socket options for all HTTP connections.
+
+    Example:
+        from posthog import set_socket_options
+        set_socket_options([(socket.SOL_SOCKET, socket.SO_KEEPALIVE, 1)])
+    """
+    global _session, _flags_session, _socket_options
+    if socket_options == _socket_options:
+        return
+    _socket_options = socket_options
+    _session = _build_session(socket_options)
+    _flags_session = _build_flags_session(socket_options)
+
+
+def enable_keep_alive() -> None:
+    """Enable TCP keepalive to prevent idle connections from being dropped."""
+    set_socket_options(KEEP_ALIVE_SOCKET_OPTIONS)
+
+
+def disable_connection_reuse() -> None:
+    """Disable connection reuse, creating a fresh connection for each request."""
+    global _pooling_enabled
+    _pooling_enabled = False
+
 
 US_INGESTION_ENDPOINT = "https://us.i.posthog.com"
 EU_INGESTION_ENDPOINT = "https://eu.i.posthog.com"
@@ -43,7 +178,13 @@ def determine_server_host(host: Optional[str]) -> str:
 
 
 def post(
-    api_key: str, host: Optional[str] = None, path=None, gzip: bool = False, timeout: int = 15, **kwargs
+    api_key: str,
+    host: Optional[str] = None,
+    path=None,
+    gzip: bool = False,
+    timeout: int = 15,
+    session: Optional[requests.Session] = None,
+    **kwargs,
 ) -> requests.Response:
     """Post the `kwargs` to the API"""
     log = logging.getLogger("posthog")
@@ -63,7 +204,9 @@ def post(
             gz.write(data.encode("utf-8"))
         data = buf.getvalue()
 
-    res = _session.post(url, data=data, headers=headers, timeout=timeout)
+    res = (session or _get_session()).post(
+        url, data=data, headers=headers, timeout=timeout
+    )
 
     if res.status_code == 200:
         log.debug("data uploaded successfully")
@@ -100,35 +243,108 @@ def _process_response(
         raise APIError(res.status_code, res.text)
 
 
-def decide(api_key: str, host: Optional[str] = None, gzip: bool = False, timeout: int = 15, **kwargs) -> Any:
+def decide(
+    api_key: str,
+    host: Optional[str] = None,
+    gzip: bool = False,
+    timeout: int = 15,
+    **kwargs,
+) -> Any:
     """Post the `kwargs to the decide API endpoint"""
     res = post(api_key, host, "/decide/?v=4", gzip, timeout, **kwargs)
     return _process_response(res, success_message="Feature flags decided successfully")
 
 
-def flags(api_key: str, host: Optional[str] = None, gzip: bool = False, timeout: int = 15, **kwargs) -> Any:
-    """Post the `kwargs to the flags API endpoint"""
-    res = post(api_key, host, "/flags/?v=2", gzip, timeout, **kwargs)
-    return _process_response(res, success_message="Feature flags evaluated successfully")
+def flags(
+    api_key: str,
+    host: Optional[str] = None,
+    gzip: bool = False,
+    timeout: int = 15,
+    **kwargs,
+) -> Any:
+    """Post the kwargs to the flags API endpoint with automatic retries."""
+    res = post(
+        api_key,
+        host,
+        "/flags/?v=2",
+        gzip,
+        timeout,
+        session=_get_flags_session(),
+        **kwargs,
+    )
+    return _process_response(
+        res, success_message="Feature flags evaluated successfully"
+    )
 
 
-def remote_config(personal_api_key: str, host: Optional[str] = None, key: str = "", timeout: int = 15) -> Any:
+def remote_config(
+    personal_api_key: str,
+    project_api_key: str,
+    host: Optional[str] = None,
+    key: str = "",
+    timeout: int = 15,
+) -> Any:
     """Get remote config flag value from remote_config API endpoint"""
-    return get(personal_api_key, f"/api/projects/@current/feature_flags/{key}/remote_config/", host, timeout)
+    response = get(
+        personal_api_key,
+        f"/api/projects/@current/feature_flags/{key}/remote_config?token={project_api_key}",
+        host,
+        timeout,
+    )
+    return response.data
 
 
 def batch_post(
-    api_key: str, host: Optional[str] = None, gzip: bool = False, timeout: int = 15, **kwargs
+    api_key: str,
+    host: Optional[str] = None,
+    gzip: bool = False,
+    timeout: int = 15,
+    **kwargs,
 ) -> requests.Response:
     """Post the `kwargs` to the batch API endpoint for events"""
     res = post(api_key, host, "/batch/", gzip, timeout, **kwargs)
-    return _process_response(res, success_message="data uploaded successfully", return_json=False)
+    return _process_response(
+        res, success_message="data uploaded successfully", return_json=False
+    )
 
 
-def get(api_key: str, url: str, host: Optional[str] = None, timeout: Optional[int] = None) -> requests.Response:
-    url = remove_trailing_slash(host or DEFAULT_HOST) + url
-    res = requests.get(url, headers={"Authorization": "Bearer %s" % api_key, "User-Agent": USER_AGENT}, timeout=timeout)
-    return _process_response(res, success_message=f"GET {url} completed successfully")
+def get(
+    api_key: str,
+    url: str,
+    host: Optional[str] = None,
+    timeout: Optional[int] = None,
+    etag: Optional[str] = None,
+) -> GetResponse:
+    """
+    Make a GET request with optional ETag support.
+
+    If an etag is provided, sends If-None-Match header. Returns GetResponse with:
+    - not_modified=True and data=None if server returns 304
+    - not_modified=False and data=response if server returns 200
+    """
+    log = logging.getLogger("posthog")
+    full_url = remove_trailing_slash(host or DEFAULT_HOST) + url
+    headers = {"Authorization": "Bearer %s" % api_key, "User-Agent": USER_AGENT}
+
+    if etag:
+        headers["If-None-Match"] = etag
+
+    res = _get_session().get(full_url, headers=headers, timeout=timeout)
+
+    masked_url = _mask_tokens_in_url(full_url)
+
+    # Handle 304 Not Modified
+    if res.status_code == 304:
+        log.debug(f"GET {masked_url} returned 304 Not Modified")
+        response_etag = res.headers.get("ETag")
+        return GetResponse(data=None, etag=response_etag or etag, not_modified=True)
+
+    # Handle normal response
+    data = _process_response(
+        res, success_message=f"GET {masked_url} completed successfully"
+    )
+    response_etag = res.headers.get("ETag")
+    return GetResponse(data=data, etag=response_etag, not_modified=False)
 
 
 class APIError(Exception):
@@ -145,6 +361,12 @@ class QuotaLimitError(APIError):
     pass
 
 
+# Re-export requests exceptions for use in client.py
+# This keeps all requests library imports centralized in this module
+RequestsTimeout = requests.exceptions.Timeout
+RequestsConnectionError = requests.exceptions.ConnectionError
+
+
 class DatetimeSerializer(json.JSONEncoder):
     def default(self, obj: Any):
         if isinstance(obj, (date, datetime)):

posthog/sentry/__init__.py

@@ -1 +0,0 @@
-POSTHOG_ID_TAG = "posthog_distinct_id"

posthog/sentry/django.py

@@ -1,28 +0,0 @@
-from django.conf import settings
-from sentry_sdk import configure_scope
-
-from posthog.sentry import POSTHOG_ID_TAG
-
-GET_DISTINCT_ID = getattr(settings, "POSTHOG_DJANGO", {}).get("distinct_id")
-
-
-def get_distinct_id(request):
-    if not GET_DISTINCT_ID:
-        return None
-    try:
-        return GET_DISTINCT_ID(request)
-    except:  # noqa: E722
-        return None
-
-
-class PosthogDistinctIdMiddleware:
-    def __init__(self, get_response):
-        self.get_response = get_response
-
-    def __call__(self, request):
-        with configure_scope() as scope:
-            distinct_id = get_distinct_id(request)
-            if distinct_id:
-                scope.set_tag(POSTHOG_ID_TAG, distinct_id)
-            response = self.get_response(request)
-        return response

posthog/sentry/posthog_integration.py

@@ -1,52 +0,0 @@
-from sentry_sdk._types import MYPY
-from sentry_sdk.hub import Hub
-from sentry_sdk.integrations import Integration
-from sentry_sdk.scope import add_global_event_processor
-from sentry_sdk.utils import Dsn
-
-import posthog
-from posthog.request import DEFAULT_HOST
-from posthog.sentry import POSTHOG_ID_TAG
-
-if MYPY:
-    from typing import Optional  # noqa: F401
-
-    from sentry_sdk._types import Event, Hint  # noqa: F401
-
-
-class PostHogIntegration(Integration):
-    identifier = "posthog-python"
-    organization = None  # The Sentry organization, used to send a direct link from PostHog to Sentry
-    project_id = None  # The Sentry project id, used to send a direct link from PostHog to Sentry
-    prefix = "https://sentry.io/organizations/"  # URL of a hosted sentry instance (default: https://sentry.io/organizations/)
-
-    @staticmethod
-    def setup_once():
-        @add_global_event_processor
-        def processor(event, hint):
-            # type: (Event, Optional[Hint]) -> Optional[Event]
-            if Hub.current.get_integration(PostHogIntegration) is not None:
-                if event.get("level") != "error":
-                    return event
-
-                if event.get("tags", {}).get(POSTHOG_ID_TAG):
-                    posthog_distinct_id = event["tags"][POSTHOG_ID_TAG]
-                    event["tags"]["PostHog URL"] = f"{posthog.host or DEFAULT_HOST}/person/{posthog_distinct_id}"
-
-                    properties = {
-                        "$sentry_event_id": event["event_id"],
-                        "$sentry_exception": event["exception"],
-                    }
-
-                    if PostHogIntegration.organization:
-                        project_id = PostHogIntegration.project_id or (
-                            not not Hub.current.client.dsn and Dsn(Hub.current.client.dsn).project_id
-                        )
-                        if project_id:
-                            properties["$sentry_url"] = (
-                                f"{PostHogIntegration.prefix}{PostHogIntegration.organization}/issues/?project={project_id}&query={event['event_id']}"
-                            )
-
-                    posthog.capture(posthog_distinct_id, "$exception", properties)
-
-            return event

posthog/test/ai/gemini/test_gemini_async.py

@@ -0,0 +1,853 @@
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+try:
+    from google import genai as google_genai
+
+    from posthog.ai.gemini import AsyncClient
+
+    GEMINI_AVAILABLE = True
+except ImportError:
+    GEMINI_AVAILABLE = False
+
+pytestmark = [
+    pytest.mark.skipif(
+        not GEMINI_AVAILABLE, reason="Google Gemini package is not available"
+    ),
+    pytest.mark.asyncio,
+]
+
+
+@pytest.fixture
+def mock_client():
+    with patch("posthog.client.Client") as mock_client:
+        mock_client.privacy_mode = False
+        yield mock_client
+
+
+@pytest.fixture
+def mock_gemini_response():
+    mock_response = MagicMock()
+    mock_response.text = "Test response from Gemini"
+
+    mock_usage = MagicMock()
+    mock_usage.prompt_token_count = 20
+    mock_usage.candidates_token_count = 10
+    # Ensure cache and reasoning tokens are not present (not MagicMock)
+    mock_usage.cached_content_token_count = 0
+    mock_usage.thoughts_token_count = 0
+    mock_response.usage_metadata = mock_usage
+
+    mock_candidate = MagicMock()
+    mock_candidate.text = "Test response from Gemini"
+    mock_content = MagicMock()
+    mock_part = MagicMock()
+    mock_part.text = "Test response from Gemini"
+    mock_content.parts = [mock_part]
+    mock_candidate.content = mock_content
+    mock_response.candidates = [mock_candidate]
+
+    return mock_response
+
+
+@pytest.fixture
+def mock_google_genai_client():
+    """Mock for the google-genai Client with async support"""
+    with patch.object(google_genai, "Client") as mock_client_class:
+        mock_client_instance = MagicMock()
+        mock_models = MagicMock()
+        mock_aio = MagicMock()
+        mock_aio_models = MagicMock()
+
+        mock_client_instance.models = mock_models
+        mock_client_instance.aio = mock_aio
+        mock_aio.models = mock_aio_models
+
+        mock_client_class.return_value = mock_client_instance
+        yield mock_client_instance
+
+
+@pytest.fixture
+def mock_gemini_response_with_function_calls():
+    mock_response = MagicMock()
+
+    # Mock usage metadata
+    mock_usage = MagicMock()
+    mock_usage.prompt_token_count = 25
+    mock_usage.candidates_token_count = 15
+    mock_usage.cached_content_token_count = 0
+    mock_usage.thoughts_token_count = 0
+    mock_response.usage_metadata = mock_usage
+
+    # Mock function call
+    mock_function_call = MagicMock()
+    mock_function_call.name = "get_current_weather"
+    mock_function_call.args = {"location": "San Francisco"}
+
+    # Mock text part 1
+    mock_text_part1 = MagicMock()
+    mock_text_part1.text = "I'll check the weather for you."
+    type(mock_text_part1).text = mock_text_part1.text
+
+    # Mock text part 2
+    mock_text_part2 = MagicMock()
+    mock_text_part2.text = " Let me look that up."
+    type(mock_text_part2).text = mock_text_part2.text
+
+    # Mock function call part
+    mock_function_part = MagicMock()
+    mock_function_part.function_call = mock_function_call
+    type(mock_function_part).function_call = mock_function_part.function_call
+    del mock_function_part.text
+
+    # Mock content with 2 text parts and 1 function call part
+    mock_content = MagicMock()
+    mock_content.parts = [mock_text_part1, mock_text_part2, mock_function_part]
+
+    # Mock candidate
+    mock_candidate = MagicMock()
+    mock_candidate.content = mock_content
+    mock_response.candidates = [mock_candidate]
+
+    return mock_response
+
+
+async def test_async_client_basic_generation(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test the async Client/AsyncModels API structure"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Tell me a fun fact about hedgehogs"],
+        posthog_distinct_id="test-id",
+        posthog_properties={"foo": "bar"},
+    )
+
+    assert response == mock_gemini_response
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    assert call_args["distinct_id"] == "test-id"
+    assert call_args["event"] == "$ai_generation"
+    assert props["$ai_provider"] == "gemini"
+    assert props["$ai_model"] == "gemini-2.0-flash"
+    assert props["$ai_input_tokens"] == 20
+    assert props["$ai_output_tokens"] == 10
+    assert props["foo"] == "bar"
+    assert "$ai_trace_id" in props
+    assert props["$ai_latency"] > 0
+
+
+async def test_async_client_streaming_with_generate_content_stream(
+    mock_client, mock_google_genai_client
+):
+    """Test the async generate_content_stream method"""
+
+    async def mock_streaming_response():
+        mock_chunk1 = MagicMock()
+        mock_chunk1.text = "Hello "
+        mock_usage1 = MagicMock()
+        mock_usage1.prompt_token_count = 10
+        mock_usage1.candidates_token_count = 5
+        mock_usage1.cached_content_token_count = 0
+        mock_usage1.thoughts_token_count = 0
+        mock_chunk1.usage_metadata = mock_usage1
+        yield mock_chunk1
+
+        mock_chunk2 = MagicMock()
+        mock_chunk2.text = "world!"
+        mock_usage2 = MagicMock()
+        mock_usage2.prompt_token_count = 10
+        mock_usage2.candidates_token_count = 10
+        mock_usage2.cached_content_token_count = 0
+        mock_usage2.thoughts_token_count = 0
+        mock_chunk2.usage_metadata = mock_usage2
+        yield mock_chunk2
+
+    # Mock the async generate_content_stream method
+    mock_google_genai_client.aio.models.generate_content_stream = AsyncMock(
+        return_value=mock_streaming_response()
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content_stream(
+        model="gemini-2.0-flash",
+        contents=["Write a short story"],
+        posthog_distinct_id="test-id",
+        posthog_properties={"feature": "streaming"},
+    )
+
+    chunks = []
+    async for chunk in response:
+        chunks.append(chunk)
+
+    assert len(chunks) == 2
+    assert chunks[0].text == "Hello "
+    assert chunks[1].text == "world!"
+
+    # Check that the streaming event was captured
+    assert mock_client.capture.call_count == 1
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    assert call_args["distinct_id"] == "test-id"
+    assert call_args["event"] == "$ai_generation"
+    assert props["$ai_provider"] == "gemini"
+    assert props["$ai_model"] == "gemini-2.0-flash"
+    assert props["$ai_input_tokens"] == 10
+    assert props["$ai_output_tokens"] == 10
+    assert props["feature"] == "streaming"
+    assert isinstance(props["$ai_latency"], float)
+
+
+async def test_async_client_streaming_with_tools(mock_client, mock_google_genai_client):
+    """Test that tools are captured in async streaming mode"""
+
+    async def mock_streaming_response():
+        mock_chunk1 = MagicMock()
+        mock_chunk1.text = "I'll check "
+        mock_usage1 = MagicMock()
+        mock_usage1.prompt_token_count = 15
+        mock_usage1.candidates_token_count = 5
+        mock_usage1.cached_content_token_count = 0
+        mock_usage1.thoughts_token_count = 0
+        mock_chunk1.usage_metadata = mock_usage1
+        yield mock_chunk1
+
+        mock_chunk2 = MagicMock()
+        mock_chunk2.text = "the weather"
+        mock_usage2 = MagicMock()
+        mock_usage2.prompt_token_count = 15
+        mock_usage2.candidates_token_count = 10
+        mock_usage2.cached_content_token_count = 0
+        mock_usage2.thoughts_token_count = 0
+        mock_chunk2.usage_metadata = mock_usage2
+        yield mock_chunk2
+
+    # Mock the async generate_content_stream method
+    mock_google_genai_client.aio.models.generate_content_stream = AsyncMock(
+        return_value=mock_streaming_response()
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    # Create mock tools configuration
+    mock_tool = MagicMock()
+    mock_tool.function_declarations = [
+        MagicMock(
+            name="get_current_weather",
+            description="Gets the current weather for a given location.",
+            parameters=MagicMock(
+                type="OBJECT",
+                properties={
+                    "location": MagicMock(
+                        type="STRING",
+                        description="The city and state, e.g. San Francisco, CA",
+                    )
+                },
+                required=["location"],
+            ),
+        )
+    ]
+
+    mock_config = MagicMock()
+    mock_config.tools = [mock_tool]
+
+    response = await client.models.generate_content_stream(
+        model="gemini-2.0-flash",
+        contents=["What's the weather in SF?"],
+        config=mock_config,
+        posthog_distinct_id="test-id",
+        posthog_properties={"feature": "streaming_with_tools"},
+    )
+
+    chunks = []
+    async for chunk in response:
+        chunks.append(chunk)
+
+    assert len(chunks) == 2
+    assert chunks[0].text == "I'll check "
+    assert chunks[1].text == "the weather"
+
+    # Check that the streaming event was captured with tools
+    assert mock_client.capture.call_count == 1
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    assert call_args["distinct_id"] == "test-id"
+    assert call_args["event"] == "$ai_generation"
+    assert props["$ai_provider"] == "gemini"
+    assert props["$ai_model"] == "gemini-2.0-flash"
+    assert props["$ai_input_tokens"] == 15
+    assert props["$ai_output_tokens"] == 10
+    assert props["feature"] == "streaming_with_tools"
+    assert isinstance(props["$ai_latency"], float)
+
+    # Verify that tools are captured in the $ai_tools property in streaming mode
+    assert props["$ai_tools"] == [mock_tool]
+
+
+async def test_async_client_groups(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test groups functionality with async Client API"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Hello"],
+        posthog_distinct_id="test-id",
+        posthog_groups={"company": "company_123"},
+    )
+
+    call_args = mock_client.capture.call_args[1]
+    assert call_args["groups"] == {"company": "company_123"}
+
+
+async def test_async_client_privacy_mode_local(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test local privacy mode with async Client API"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Hello"],
+        posthog_distinct_id="test-id",
+        posthog_privacy_mode=True,
+    )
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] is None
+    assert props["$ai_output_choices"] is None
+
+
+async def test_async_client_privacy_mode_global(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test global privacy mode with async Client API"""
+    mock_client.privacy_mode = True
+
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Hello"],
+        posthog_distinct_id="test-id",
+    )
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] is None
+    assert props["$ai_output_choices"] is None
+
+
+async def test_async_client_different_input_formats(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test different input formats with async Client API"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    # Test string input
+    await client.models.generate_content(
+        model="gemini-2.0-flash", contents="Hello", posthog_distinct_id="test-id"
+    )
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] == [{"role": "user", "content": "Hello"}]
+
+    # Test Gemini-specific format with parts array
+    mock_client.reset_mock()
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=[{"role": "user", "parts": [{"text": "hey"}]}],
+        posthog_distinct_id="test-id",
+    )
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] == [
+        {"role": "user", "content": [{"type": "text", "text": "hey"}]}
+    ]
+
+    # Test multiple parts in the parts array
+    mock_client.reset_mock()
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=[{"role": "user", "parts": [{"text": "Hello "}, {"text": "world"}]}],
+        posthog_distinct_id="test-id",
+    )
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] == [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Hello "},
+                {"type": "text", "text": "world"},
+            ],
+        }
+    ]
+
+    # Test list input with string
+    mock_client.capture.reset_mock()
+    await client.models.generate_content(
+        model="gemini-2.0-flash", contents=["List item"], posthog_distinct_id="test-id"
+    )
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_input"] == [{"role": "user", "content": "List item"}]
+
+
+async def test_async_client_model_parameters(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test model parameters with async Client API"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Hello"],
+        posthog_distinct_id="test-id",
+        temperature=0.7,
+        max_tokens=100,
+    )
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+    assert props["$ai_model_parameters"]["temperature"] == 0.7
+    assert props["$ai_model_parameters"]["max_tokens"] == 100
+
+
+async def test_async_client_default_settings(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test async client with default PostHog settings"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(
+        api_key="test-key",
+        posthog_client=mock_client,
+        posthog_distinct_id="default_user",
+        posthog_properties={"team": "ai"},
+        posthog_privacy_mode=False,
+        posthog_groups={"company": "acme_corp"},
+    )
+
+    # Call without overriding defaults
+    await client.models.generate_content(model="gemini-2.0-flash", contents=["Hello"])
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    assert call_args["distinct_id"] == "default_user"
+    assert call_args["groups"] == {"company": "acme_corp"}
+    assert props["team"] == "ai"
+
+
+async def test_async_client_override_defaults(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test overriding async client defaults per call"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    client = AsyncClient(
+        api_key="test-key",
+        posthog_client=mock_client,
+        posthog_distinct_id="default_user",
+        posthog_properties={"team": "ai"},
+        posthog_privacy_mode=False,
+        posthog_groups={"company": "acme_corp"},
+    )
+
+    # Override defaults in call
+    await client.models.generate_content(
+        model="gemini-2.0-flash",
+        contents=["Hello"],
+        posthog_distinct_id="specific_user",
+        posthog_properties={"feature": "chat", "urgent": True},
+        posthog_privacy_mode=True,
+        posthog_groups={"organization": "special_org"},
+    )
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    # Check overrides
+    assert call_args["distinct_id"] == "specific_user"
+    assert call_args["groups"] == {"organization": "special_org"}
+    assert props["$ai_input"] is None  # privacy mode was overridden
+
+    # Check merged properties (defaults + call-specific)
+    assert props["team"] == "ai"  # from defaults
+    assert props["feature"] == "chat"  # from call
+    assert props["urgent"] is True  # from call
+
+
+async def test_async_vertex_ai_parameters_passed_through(
+    mock_client, mock_google_genai_client, mock_gemini_response
+):
+    """Test that Vertex AI parameters are properly passed to genai.Client"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response
+    )
+
+    # Mock credentials object
+    mock_credentials = MagicMock()
+    mock_debug_config = MagicMock()
+    mock_http_options = MagicMock()
+
+    # Create client with Vertex AI parameters
+    AsyncClient(
+        vertexai=True,
+        credentials=mock_credentials,
+        project="test-project",
+        location="us-central1",
+        debug_config=mock_debug_config,
+        http_options=mock_http_options,
+        posthog_client=mock_client,
+    )
+
+    # Verify genai.Client was called with correct parameters
+    google_genai.Client.assert_called_once_with(
+        vertexai=True,
+        credentials=mock_credentials,
+        project="test-project",
+        location="us-central1",
+        debug_config=mock_debug_config,
+        http_options=mock_http_options,
+    )
+
+
+async def test_async_api_key_mode(mock_client, mock_google_genai_client):
+    """Test API key authentication mode with async client"""
+
+    # Create async client with just API key (traditional mode)
+    AsyncClient(
+        api_key="test-api-key",
+        posthog_client=mock_client,
+    )
+
+    # Verify genai.Client was called with only api_key
+    google_genai.Client.assert_called_once_with(api_key="test-api-key")
+
+
+async def test_async_function_calls_in_output_choices(
+    mock_client, mock_google_genai_client, mock_gemini_response_with_function_calls
+):
+    """Test that function calls are properly included in $ai_output_choices with async"""
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_gemini_response_with_function_calls
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content(
+        model="gemini-2.5-flash",
+        contents=["What's the weather in San Francisco?"],
+        posthog_distinct_id="test-id",
+    )
+
+    assert response == mock_gemini_response_with_function_calls
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    assert call_args["distinct_id"] == "test-id"
+    assert call_args["event"] == "$ai_generation"
+    assert props["$ai_provider"] == "gemini"
+    assert props["$ai_model"] == "gemini-2.5-flash"
+    assert props["$ai_output_choices"] == [
+        {
+            "role": "assistant",
+            "content": [
+                {"type": "text", "text": "I'll check the weather for you."},
+                {"type": "text", "text": " Let me look that up."},
+                {
+                    "type": "function",
+                    "function": {
+                        "name": "get_current_weather",
+                        "arguments": {"location": "San Francisco"},
+                    },
+                },
+            ],
+        }
+    ]
+
+    # Check token usage
+    assert props["$ai_input_tokens"] == 25
+    assert props["$ai_output_tokens"] == 15
+    assert props["$ai_http_status"] == 200
+
+
+async def test_async_cache_and_reasoning_tokens(mock_client, mock_google_genai_client):
+    """Test that cache and reasoning tokens are properly extracted with async"""
+    # Create a mock response with cache and reasoning tokens
+    mock_response = MagicMock()
+    mock_response.text = "Test response with cache"
+
+    mock_usage = MagicMock()
+    mock_usage.prompt_token_count = 100
+    mock_usage.candidates_token_count = 50
+    mock_usage.cached_content_token_count = 30  # Cache tokens
+    mock_usage.thoughts_token_count = 10  # Reasoning tokens
+    mock_response.usage_metadata = mock_usage
+
+    # Mock candidates
+    mock_candidate = MagicMock()
+    mock_candidate.text = "Test response with cache"
+    mock_response.candidates = [mock_candidate]
+
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content(
+        model="gemini-2.5-pro",
+        contents="Test with cache",
+        posthog_distinct_id="test-id",
+    )
+
+    assert response == mock_response
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    # Check that all token types are present
+    assert props["$ai_input_tokens"] == 100
+    assert props["$ai_output_tokens"] == 50
+    assert props["$ai_cache_read_input_tokens"] == 30
+    assert props["$ai_reasoning_tokens"] == 10
+
+
+async def test_async_streaming_cache_and_reasoning_tokens(
+    mock_client, mock_google_genai_client
+):
+    """Test that cache and reasoning tokens are properly extracted in async streaming"""
+
+    async def mock_streaming_response():
+        # Create mock chunks with cache and reasoning tokens
+        chunk1 = MagicMock()
+        chunk1.text = "Hello "
+        chunk1_usage = MagicMock()
+        chunk1_usage.prompt_token_count = 100
+        chunk1_usage.candidates_token_count = 5
+        chunk1_usage.cached_content_token_count = 30  # Cache tokens
+        chunk1_usage.thoughts_token_count = 0
+        chunk1.usage_metadata = chunk1_usage
+        yield chunk1
+
+        chunk2 = MagicMock()
+        chunk2.text = "world!"
+        chunk2_usage = MagicMock()
+        chunk2_usage.prompt_token_count = 100
+        chunk2_usage.candidates_token_count = 10
+        chunk2_usage.cached_content_token_count = 30  # Same cache tokens
+        chunk2_usage.thoughts_token_count = 5  # Reasoning tokens
+        chunk2.usage_metadata = chunk2_usage
+        yield chunk2
+
+    mock_google_genai_client.aio.models.generate_content_stream = AsyncMock(
+        return_value=mock_streaming_response()
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content_stream(
+        model="gemini-2.5-pro",
+        contents="Test streaming with cache",
+        posthog_distinct_id="test-id",
+    )
+
+    # Consume the stream
+    result = []
+    async for chunk in response:
+        result.append(chunk)
+
+    assert len(result) == 2
+
+    # Check PostHog capture was called
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    # Check that all token types are present (should use final chunk's usage)
+    assert props["$ai_input_tokens"] == 100
+    assert props["$ai_output_tokens"] == 10
+    assert props["$ai_cache_read_input_tokens"] == 30
+    assert props["$ai_reasoning_tokens"] == 5
+
+
+async def test_async_web_search_grounding(mock_client, mock_google_genai_client):
+    """Test async web search detection via grounding_metadata."""
+
+    # Create mock response with grounding metadata
+    mock_response = MagicMock()
+
+    # Mock usage metadata
+    mock_usage = MagicMock()
+    mock_usage.prompt_token_count = 60
+    mock_usage.candidates_token_count = 40
+    mock_usage.cached_content_token_count = 0
+    mock_usage.thoughts_token_count = 0
+    mock_response.usage_metadata = mock_usage
+
+    # Mock grounding metadata
+    mock_grounding_chunk = MagicMock()
+    mock_grounding_chunk.uri = "https://example.com"
+
+    mock_grounding_metadata = MagicMock()
+    mock_grounding_metadata.grounding_chunks = [mock_grounding_chunk]
+
+    # Mock text part
+    mock_text_part = MagicMock()
+    mock_text_part.text = "According to search results..."
+    type(mock_text_part).text = mock_text_part.text
+
+    # Mock content with parts
+    mock_content = MagicMock()
+    mock_content.parts = [mock_text_part]
+
+    # Mock candidate with grounding metadata
+    mock_candidate = MagicMock()
+    mock_candidate.content = mock_content
+    mock_candidate.grounding_metadata = mock_grounding_metadata
+    type(mock_candidate).grounding_metadata = mock_candidate.grounding_metadata
+
+    mock_response.candidates = [mock_candidate]
+    mock_response.text = "According to search results..."
+
+    # Mock the async generate_content method
+    mock_google_genai_client.aio.models.generate_content = AsyncMock(
+        return_value=mock_response
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+    response = await client.models.generate_content(
+        model="gemini-2.5-flash",
+        contents="What's the latest news?",
+        posthog_distinct_id="test-id",
+    )
+
+    assert response == mock_response
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    # Verify web search count is detected (binary for grounding)
+    assert props["$ai_web_search_count"] == 1
+    assert props["$ai_input_tokens"] == 60
+    assert props["$ai_output_tokens"] == 40
+
+
+async def test_async_streaming_with_web_search(mock_client, mock_google_genai_client):
+    """Test that web search count is properly captured in async streaming mode."""
+
+    async def mock_streaming_response():
+        # Create chunk 1 with grounding metadata
+        mock_chunk1 = MagicMock()
+        mock_chunk1.text = "According to "
+
+        mock_usage1 = MagicMock()
+        mock_usage1.prompt_token_count = 30
+        mock_usage1.candidates_token_count = 5
+        mock_usage1.cached_content_token_count = 0
+        mock_usage1.thoughts_token_count = 0
+        mock_chunk1.usage_metadata = mock_usage1
+
+        # Add grounding metadata to first chunk
+        mock_grounding_chunk = MagicMock()
+        mock_grounding_chunk.uri = "https://example.com"
+
+        mock_grounding_metadata = MagicMock()
+        mock_grounding_metadata.grounding_chunks = [mock_grounding_chunk]
+
+        mock_candidate1 = MagicMock()
+        mock_candidate1.grounding_metadata = mock_grounding_metadata
+        type(mock_candidate1).grounding_metadata = mock_candidate1.grounding_metadata
+
+        mock_chunk1.candidates = [mock_candidate1]
+        yield mock_chunk1
+
+        # Create chunk 2
+        mock_chunk2 = MagicMock()
+        mock_chunk2.text = "search results..."
+
+        mock_usage2 = MagicMock()
+        mock_usage2.prompt_token_count = 30
+        mock_usage2.candidates_token_count = 15
+        mock_usage2.cached_content_token_count = 0
+        mock_usage2.thoughts_token_count = 0
+        mock_chunk2.usage_metadata = mock_usage2
+
+        mock_candidate2 = MagicMock()
+        mock_chunk2.candidates = [mock_candidate2]
+        yield mock_chunk2
+
+    # Mock the async generate_content_stream method
+    mock_google_genai_client.aio.models.generate_content_stream = AsyncMock(
+        return_value=mock_streaming_response()
+    )
+
+    client = AsyncClient(api_key="test-key", posthog_client=mock_client)
+
+    response = await client.models.generate_content_stream(
+        model="gemini-2.5-flash",
+        contents="What's the latest news?",
+        posthog_distinct_id="test-id",
+    )
+
+    chunks = []
+    async for chunk in response:
+        chunks.append(chunk)
+
+    assert len(chunks) == 2
+    assert mock_client.capture.call_count == 1
+
+    call_args = mock_client.capture.call_args[1]
+    props = call_args["properties"]
+
+    # Verify web search count is detected (binary for grounding)
+    assert props["$ai_web_search_count"] == 1
+    assert props["$ai_input_tokens"] == 30
+    assert props["$ai_output_tokens"] == 15

posthog/test/ai/langchain/__init__.py

@@ -1,5 +1,5 @@
 import pytest
 
-pytest.importorskip("langchain")
+pytest.importorskip("langchain_core")
 pytest.importorskip("langchain_community")
 pytest.importorskip("langgraph")

posthog/test/ai/test_sanitization.py

@@ -0,0 +1,522 @@
+import os
+import unittest
+
+from posthog.ai.sanitization import (
+    redact_base64_data_url,
+    sanitize_openai,
+    sanitize_openai_response,
+    sanitize_anthropic,
+    sanitize_gemini,
+    sanitize_langchain,
+    is_base64_data_url,
+    is_raw_base64,
+    REDACTED_IMAGE_PLACEHOLDER,
+)
+
+
+class TestSanitization(unittest.TestCase):
+    def setUp(self):
+        self.sample_base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        self.sample_base64_png = "data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAUA..."
+        self.regular_url = "https://example.com/image.jpg"
+        self.raw_base64 = "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUl=="
+
+    def test_is_base64_data_url(self):
+        self.assertTrue(is_base64_data_url(self.sample_base64_image))
+        self.assertTrue(is_base64_data_url(self.sample_base64_png))
+        self.assertFalse(is_base64_data_url(self.regular_url))
+        self.assertFalse(is_base64_data_url("regular text"))
+
+    def test_is_raw_base64(self):
+        self.assertTrue(is_raw_base64(self.raw_base64))
+        self.assertFalse(is_raw_base64("short"))
+        self.assertFalse(is_raw_base64(self.regular_url))
+        self.assertFalse(is_raw_base64("/path/to/file"))
+
+    def test_redact_base64_data_url(self):
+        self.assertEqual(
+            redact_base64_data_url(self.sample_base64_image), REDACTED_IMAGE_PLACEHOLDER
+        )
+        self.assertEqual(
+            redact_base64_data_url(self.sample_base64_png), REDACTED_IMAGE_PLACEHOLDER
+        )
+        self.assertEqual(redact_base64_data_url(self.regular_url), self.regular_url)
+        self.assertEqual(redact_base64_data_url(None), None)
+        self.assertEqual(redact_base64_data_url(123), 123)
+
+    def test_sanitize_openai(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "What is in this image?"},
+                    {
+                        "type": "image_url",
+                        "image_url": {
+                            "url": self.sample_base64_image,
+                            "detail": "high",
+                        },
+                    },
+                ],
+            }
+        ]
+
+        result = sanitize_openai(input_data)
+
+        self.assertEqual(result[0]["content"][0]["text"], "What is in this image?")
+        self.assertEqual(
+            result[0]["content"][1]["image_url"]["url"], REDACTED_IMAGE_PLACEHOLDER
+        )
+        self.assertEqual(result[0]["content"][1]["image_url"]["detail"], "high")
+
+    def test_sanitize_openai_preserves_regular_urls(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image_url",
+                        "image_url": {"url": self.regular_url},
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_openai(input_data)
+        self.assertEqual(result[0]["content"][0]["image_url"]["url"], self.regular_url)
+
+    def test_sanitize_openai_response(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "input_image",
+                        "image_url": self.sample_base64_image,
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_openai_response(input_data)
+        self.assertEqual(
+            result[0]["content"][0]["image_url"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+    def test_sanitize_anthropic(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "What is in this image?"},
+                    {
+                        "type": "image",
+                        "source": {
+                            "type": "base64",
+                            "media_type": "image/jpeg",
+                            "data": "base64data",
+                        },
+                    },
+                ],
+            }
+        ]
+
+        result = sanitize_anthropic(input_data)
+
+        self.assertEqual(result[0]["content"][0]["text"], "What is in this image?")
+        self.assertEqual(
+            result[0]["content"][1]["source"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+        self.assertEqual(result[0]["content"][1]["source"]["type"], "base64")
+        self.assertEqual(result[0]["content"][1]["source"]["media_type"], "image/jpeg")
+
+    def test_sanitize_gemini(self):
+        input_data = [
+            {
+                "parts": [
+                    {"text": "What is in this image?"},
+                    {
+                        "inline_data": {
+                            "mime_type": "image/jpeg",
+                            "data": "base64data",
+                        }
+                    },
+                ]
+            }
+        ]
+
+        result = sanitize_gemini(input_data)
+
+        self.assertEqual(result[0]["parts"][0]["text"], "What is in this image?")
+        self.assertEqual(
+            result[0]["parts"][1]["inline_data"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+        self.assertEqual(
+            result[0]["parts"][1]["inline_data"]["mime_type"], "image/jpeg"
+        )
+
+    def test_sanitize_langchain_openai_style(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image_url",
+                        "image_url": {"url": self.sample_base64_image},
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_langchain(input_data)
+        self.assertEqual(
+            result[0]["content"][0]["image_url"]["url"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+    def test_sanitize_langchain_anthropic_style(self):
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image",
+                        "source": {"data": "base64data"},
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_langchain(input_data)
+        self.assertEqual(
+            result[0]["content"][0]["source"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+    def test_sanitize_with_data_url_format(self):
+        # Test that data URLs are properly detected and redacted across providers
+        data_url = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQABAAD"
+
+        # OpenAI format
+        openai_data = [
+            {
+                "role": "user",
+                "content": [{"type": "image_url", "image_url": {"url": data_url}}],
+            }
+        ]
+        result = sanitize_openai(openai_data)
+        self.assertEqual(
+            result[0]["content"][0]["image_url"]["url"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+        # Anthropic format
+        anthropic_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image",
+                        "source": {
+                            "type": "base64",
+                            "media_type": "image/jpeg",
+                            "data": data_url,
+                        },
+                    }
+                ],
+            }
+        ]
+        result = sanitize_anthropic(anthropic_data)
+        self.assertEqual(
+            result[0]["content"][0]["source"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+        # LangChain format
+        langchain_data = [
+            {"role": "user", "content": [{"type": "image", "data": data_url}]}
+        ]
+        result = sanitize_langchain(langchain_data)
+        self.assertEqual(result[0]["content"][0]["data"], REDACTED_IMAGE_PLACEHOLDER)
+
+    def test_sanitize_with_raw_base64(self):
+        # Test that raw base64 strings (without data URL prefix) are detected
+        raw_base64 = "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUl=="
+
+        # Test with Anthropic format
+        anthropic_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image",
+                        "source": {
+                            "type": "base64",
+                            "media_type": "image/png",
+                            "data": raw_base64,
+                        },
+                    }
+                ],
+            }
+        ]
+        result = sanitize_anthropic(anthropic_data)
+        self.assertEqual(
+            result[0]["content"][0]["source"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+        # Test with Gemini format
+        gemini_data = [
+            {"parts": [{"inline_data": {"mime_type": "image/png", "data": raw_base64}}]}
+        ]
+        result = sanitize_gemini(gemini_data)
+        self.assertEqual(
+            result[0]["parts"][0]["inline_data"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+    def test_sanitize_preserves_regular_content(self):
+        # Ensure non-base64 content is preserved across all providers
+        regular_url = "https://example.com/image.jpg"
+        text_content = "What do you see?"
+
+        # OpenAI
+        openai_data = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": text_content},
+                    {"type": "image_url", "image_url": {"url": regular_url}},
+                ],
+            }
+        ]
+        result = sanitize_openai(openai_data)
+        self.assertEqual(result[0]["content"][0]["text"], text_content)
+        self.assertEqual(result[0]["content"][1]["image_url"]["url"], regular_url)
+
+        # Anthropic
+        anthropic_data = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": text_content},
+                    {"type": "image", "source": {"type": "url", "url": regular_url}},
+                ],
+            }
+        ]
+        result = sanitize_anthropic(anthropic_data)
+        self.assertEqual(result[0]["content"][0]["text"], text_content)
+        # URL-based images should remain unchanged
+        self.assertEqual(result[0]["content"][1]["source"]["url"], regular_url)
+
+    def test_sanitize_handles_non_dict_content(self):
+        input_data = [{"role": "user", "content": "Just text"}]
+
+        result = sanitize_openai(input_data)
+        self.assertEqual(result, input_data)
+
+    def test_sanitize_handles_none_input(self):
+        self.assertIsNone(sanitize_openai(None))
+        self.assertIsNone(sanitize_anthropic(None))
+        self.assertIsNone(sanitize_gemini(None))
+        self.assertIsNone(sanitize_langchain(None))
+
+    def test_sanitize_handles_single_message(self):
+        input_data = {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": {"url": self.sample_base64_image},
+                }
+            ],
+        }
+
+        result = sanitize_openai(input_data)
+        self.assertEqual(
+            result["content"][0]["image_url"]["url"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+
+class TestAIMultipartRequest(unittest.TestCase):
+    """Test that _INTERNAL_LLMA_MULTIMODAL environment variable controls sanitization."""
+
+    def tearDown(self):
+        # Clean up environment variable after each test
+        if "_INTERNAL_LLMA_MULTIMODAL" in os.environ:
+            del os.environ["_INTERNAL_LLMA_MULTIMODAL"]
+
+    def test_multimodal_disabled_redacts_images(self):
+        """When _INTERNAL_LLMA_MULTIMODAL is not set, images should be redacted."""
+        if "_INTERNAL_LLMA_MULTIMODAL" in os.environ:
+            del os.environ["_INTERNAL_LLMA_MULTIMODAL"]
+
+        base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        result = redact_base64_data_url(base64_image)
+        self.assertEqual(result, REDACTED_IMAGE_PLACEHOLDER)
+
+    def test_multimodal_enabled_preserves_images(self):
+        """When _INTERNAL_LLMA_MULTIMODAL is true, images should be preserved."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        result = redact_base64_data_url(base64_image)
+        self.assertEqual(result, base64_image)
+
+    def test_multimodal_enabled_with_1(self):
+        """_INTERNAL_LLMA_MULTIMODAL=1 should enable multimodal."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "1"
+
+        base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        result = redact_base64_data_url(base64_image)
+        self.assertEqual(result, base64_image)
+
+    def test_multimodal_enabled_with_yes(self):
+        """_INTERNAL_LLMA_MULTIMODAL=yes should enable multimodal."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "yes"
+
+        base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        result = redact_base64_data_url(base64_image)
+        self.assertEqual(result, base64_image)
+
+    def test_multimodal_false_redacts_images(self):
+        """_INTERNAL_LLMA_MULTIMODAL=false should still redact."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "false"
+
+        base64_image = "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQ..."
+        result = redact_base64_data_url(base64_image)
+        self.assertEqual(result, REDACTED_IMAGE_PLACEHOLDER)
+
+    def test_anthropic_multimodal_enabled(self):
+        """Anthropic images should be preserved when _INTERNAL_LLMA_MULTIMODAL is enabled."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image",
+                        "source": {
+                            "type": "base64",
+                            "media_type": "image/jpeg",
+                            "data": "base64data",
+                        },
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_anthropic(input_data)
+        self.assertEqual(result[0]["content"][0]["source"]["data"], "base64data")
+
+    def test_gemini_multimodal_enabled(self):
+        """Gemini images should be preserved when _INTERNAL_LLMA_MULTIMODAL is enabled."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        input_data = [
+            {
+                "parts": [
+                    {"inline_data": {"mime_type": "image/jpeg", "data": "base64data"}}
+                ]
+            }
+        ]
+
+        result = sanitize_gemini(input_data)
+        self.assertEqual(result[0]["parts"][0]["inline_data"]["data"], "base64data")
+
+    def test_langchain_anthropic_style_multimodal_enabled(self):
+        """LangChain Anthropic-style images should be preserved when _INTERNAL_LLMA_MULTIMODAL is enabled."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        input_data = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "type": "image",
+                        "source": {"data": "base64data"},
+                    }
+                ],
+            }
+        ]
+
+        result = sanitize_langchain(input_data)
+        self.assertEqual(result[0]["content"][0]["source"]["data"], "base64data")
+
+    def test_openai_audio_redacted_by_default(self):
+        """OpenAI audio should be redacted when _INTERNAL_LLMA_MULTIMODAL is not set."""
+        if "_INTERNAL_LLMA_MULTIMODAL" in os.environ:
+            del os.environ["_INTERNAL_LLMA_MULTIMODAL"]
+
+        input_data = [
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "audio", "data": "base64audiodata", "id": "audio_123"}
+                ],
+            }
+        ]
+
+        result = sanitize_openai(input_data)
+        self.assertEqual(result[0]["content"][0]["data"], REDACTED_IMAGE_PLACEHOLDER)
+        self.assertEqual(result[0]["content"][0]["id"], "audio_123")
+
+    def test_openai_audio_preserved_with_flag(self):
+        """OpenAI audio should be preserved when _INTERNAL_LLMA_MULTIMODAL is enabled."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        input_data = [
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "audio", "data": "base64audiodata", "id": "audio_123"}
+                ],
+            }
+        ]
+
+        result = sanitize_openai(input_data)
+        self.assertEqual(result[0]["content"][0]["data"], "base64audiodata")
+
+    def test_gemini_audio_redacted_by_default(self):
+        """Gemini audio should be redacted when _INTERNAL_LLMA_MULTIMODAL is not set."""
+        if "_INTERNAL_LLMA_MULTIMODAL" in os.environ:
+            del os.environ["_INTERNAL_LLMA_MULTIMODAL"]
+
+        input_data = [
+            {
+                "parts": [
+                    {
+                        "inline_data": {
+                            "mime_type": "audio/L16;codec=pcm;rate=24000",
+                            "data": "base64audiodata",
+                        }
+                    }
+                ]
+            }
+        ]
+
+        result = sanitize_gemini(input_data)
+        self.assertEqual(
+            result[0]["parts"][0]["inline_data"]["data"], REDACTED_IMAGE_PLACEHOLDER
+        )
+
+    def test_gemini_audio_preserved_with_flag(self):
+        """Gemini audio should be preserved when _INTERNAL_LLMA_MULTIMODAL is enabled."""
+        os.environ["_INTERNAL_LLMA_MULTIMODAL"] = "true"
+
+        input_data = [
+            {
+                "parts": [
+                    {
+                        "inline_data": {
+                            "mime_type": "audio/L16;codec=pcm;rate=24000",
+                            "data": "base64audiodata",
+                        }
+                    }
+                ]
+            }
+        ]
+
+        result = sanitize_gemini(input_data)
+        self.assertEqual(
+            result[0]["parts"][0]["inline_data"]["data"], "base64audiodata"
+        )
+
+
+if __name__ == "__main__":
+    unittest.main()

posthog/test/ai/test_system_prompts.py

@@ -0,0 +1,363 @@
+"""
+Tests for system prompt capture across all LLM providers.
+
+This test suite ensures that system prompts are correctly captured in analytics
+regardless of how they're passed to the providers:
+- As first message in messages/contents array (standard format)
+- As separate system parameter (Anthropic, OpenAI)
+- As instructions parameter (OpenAI Responses API)
+- As system_instruction parameter (Gemini)
+"""
+
+import time
+import unittest
+from unittest.mock import MagicMock, patch
+
+from posthog.client import Client
+from posthog.test.test_utils import FAKE_TEST_API_KEY
+
+
+class TestSystemPromptCapture(unittest.TestCase):
+    """Test system prompt capture for all providers."""
+
+    def setUp(self):
+        super().setUp()
+        self.test_system_prompt = "You are a helpful AI assistant."
+        self.test_user_message = "Hello, how are you?"
+        self.test_response = "I'm doing well, thank you!"
+
+        # Create mock PostHog client
+        self.client = Client(FAKE_TEST_API_KEY)
+        self.client._enqueue = MagicMock()
+        self.client.privacy_mode = False
+
+    def _assert_system_prompt_captured(self, captured_input):
+        """Helper to assert system prompt is correctly captured."""
+        self.assertEqual(
+            len(captured_input), 2, "Should have 2 messages (system + user)"
+        )
+        self.assertEqual(
+            captured_input[0]["role"], "system", "First message should be system"
+        )
+        self.assertEqual(
+            captured_input[0]["content"],
+            self.test_system_prompt,
+            "System content should match",
+        )
+        self.assertEqual(
+            captured_input[1]["role"], "user", "Second message should be user"
+        )
+        self.assertEqual(
+            captured_input[1]["content"],
+            self.test_user_message,
+            "User content should match",
+        )
+
+    # OpenAI Tests
+    def test_openai_messages_array_system_prompt(self):
+        """Test OpenAI with system prompt in messages array."""
+        try:
+            from openai.types.chat import ChatCompletion, ChatCompletionMessage
+            from openai.types.chat.chat_completion import Choice
+            from openai.types.completion_usage import CompletionUsage
+
+            from posthog.ai.openai import OpenAI
+        except ImportError:
+            self.skipTest("OpenAI package not available")
+
+        mock_response = ChatCompletion(
+            id="test",
+            model="gpt-4",
+            object="chat.completion",
+            created=int(time.time()),
+            choices=[
+                Choice(
+                    finish_reason="stop",
+                    index=0,
+                    message=ChatCompletionMessage(
+                        content=self.test_response, role="assistant"
+                    ),
+                )
+            ],
+            usage=CompletionUsage(
+                completion_tokens=10, prompt_tokens=20, total_tokens=30
+            ),
+        )
+
+        with patch(
+            "openai.resources.chat.completions.Completions.create",
+            return_value=mock_response,
+        ):
+            client = OpenAI(posthog_client=self.client, api_key="test")
+
+            messages = [
+                {"role": "system", "content": self.test_system_prompt},
+                {"role": "user", "content": self.test_user_message},
+            ]
+
+            client.chat.completions.create(
+                model="gpt-4", messages=messages, posthog_distinct_id="test-user"
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    def test_openai_separate_system_parameter(self):
+        """Test OpenAI with system prompt as separate parameter."""
+        try:
+            from openai.types.chat import ChatCompletion, ChatCompletionMessage
+            from openai.types.chat.chat_completion import Choice
+            from openai.types.completion_usage import CompletionUsage
+
+            from posthog.ai.openai import OpenAI
+        except ImportError:
+            self.skipTest("OpenAI package not available")
+
+        mock_response = ChatCompletion(
+            id="test",
+            model="gpt-4",
+            object="chat.completion",
+            created=int(time.time()),
+            choices=[
+                Choice(
+                    finish_reason="stop",
+                    index=0,
+                    message=ChatCompletionMessage(
+                        content=self.test_response, role="assistant"
+                    ),
+                )
+            ],
+            usage=CompletionUsage(
+                completion_tokens=10, prompt_tokens=20, total_tokens=30
+            ),
+        )
+
+        with patch(
+            "openai.resources.chat.completions.Completions.create",
+            return_value=mock_response,
+        ):
+            client = OpenAI(posthog_client=self.client, api_key="test")
+
+            messages = [{"role": "user", "content": self.test_user_message}]
+
+            client.chat.completions.create(
+                model="gpt-4",
+                messages=messages,
+                system=self.test_system_prompt,
+                posthog_distinct_id="test-user",
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    def test_openai_streaming_system_parameter(self):
+        """Test OpenAI streaming with system parameter."""
+        try:
+            from openai.types.chat.chat_completion_chunk import (
+                ChatCompletionChunk,
+                ChoiceDelta,
+            )
+            from openai.types.chat.chat_completion_chunk import Choice as ChoiceChunk
+            from openai.types.completion_usage import CompletionUsage
+
+            from posthog.ai.openai import OpenAI
+        except ImportError:
+            self.skipTest("OpenAI package not available")
+
+        chunk1 = ChatCompletionChunk(
+            id="test",
+            model="gpt-4",
+            object="chat.completion.chunk",
+            created=int(time.time()),
+            choices=[
+                ChoiceChunk(
+                    finish_reason=None,
+                    index=0,
+                    delta=ChoiceDelta(content="Hello", role="assistant"),
+                )
+            ],
+        )
+
+        chunk2 = ChatCompletionChunk(
+            id="test",
+            model="gpt-4",
+            object="chat.completion.chunk",
+            created=int(time.time()),
+            choices=[
+                ChoiceChunk(
+                    finish_reason="stop",
+                    index=0,
+                    delta=ChoiceDelta(content=" there!", role=None),
+                )
+            ],
+            usage=CompletionUsage(
+                completion_tokens=10, prompt_tokens=20, total_tokens=30
+            ),
+        )
+
+        with patch(
+            "openai.resources.chat.completions.Completions.create",
+            return_value=[chunk1, chunk2],
+        ):
+            client = OpenAI(posthog_client=self.client, api_key="test")
+
+            messages = [{"role": "user", "content": self.test_user_message}]
+
+            response_generator = client.chat.completions.create(
+                model="gpt-4",
+                messages=messages,
+                system=self.test_system_prompt,
+                stream=True,
+                posthog_distinct_id="test-user",
+            )
+
+            list(response_generator)  # Consume generator
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    # Anthropic Tests
+    def test_anthropic_messages_array_system_prompt(self):
+        """Test Anthropic with system prompt in messages array."""
+        try:
+            from posthog.ai.anthropic import Anthropic
+        except ImportError:
+            self.skipTest("Anthropic package not available")
+
+        with patch("anthropic.resources.messages.Messages.create") as mock_create:
+            mock_response = MagicMock()
+            mock_response.usage.input_tokens = 20
+            mock_response.usage.output_tokens = 10
+            mock_response.usage.cache_read_input_tokens = None
+            mock_response.usage.cache_creation_input_tokens = None
+            mock_create.return_value = mock_response
+
+            client = Anthropic(posthog_client=self.client, api_key="test")
+
+            messages = [
+                {"role": "system", "content": self.test_system_prompt},
+                {"role": "user", "content": self.test_user_message},
+            ]
+
+            client.messages.create(
+                model="claude-3-5-sonnet-20241022",
+                messages=messages,
+                posthog_distinct_id="test-user",
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    def test_anthropic_separate_system_parameter(self):
+        """Test Anthropic with system prompt as separate parameter."""
+        try:
+            from posthog.ai.anthropic import Anthropic
+        except ImportError:
+            self.skipTest("Anthropic package not available")
+
+        with patch("anthropic.resources.messages.Messages.create") as mock_create:
+            mock_response = MagicMock()
+            mock_response.usage.input_tokens = 20
+            mock_response.usage.output_tokens = 10
+            mock_response.usage.cache_read_input_tokens = None
+            mock_response.usage.cache_creation_input_tokens = None
+            mock_create.return_value = mock_response
+
+            client = Anthropic(posthog_client=self.client, api_key="test")
+
+            messages = [{"role": "user", "content": self.test_user_message}]
+
+            client.messages.create(
+                model="claude-3-5-sonnet-20241022",
+                messages=messages,
+                system=self.test_system_prompt,
+                posthog_distinct_id="test-user",
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    # Gemini Tests
+    def test_gemini_contents_array_system_prompt(self):
+        """Test Gemini with system prompt in contents array."""
+        try:
+            from posthog.ai.gemini import Client
+        except ImportError:
+            self.skipTest("Gemini package not available")
+
+        with patch("google.genai.Client") as mock_genai_class:
+            mock_response = MagicMock()
+            mock_response.candidates = [MagicMock()]
+            mock_response.candidates[0].content.parts = [MagicMock()]
+            mock_response.candidates[0].content.parts[0].text = self.test_response
+            mock_response.usage_metadata.prompt_token_count = 20
+            mock_response.usage_metadata.candidates_token_count = 10
+            mock_response.usage_metadata.cached_content_token_count = None
+            mock_response.usage_metadata.thoughts_token_count = None
+
+            mock_client_instance = MagicMock()
+            mock_models_instance = MagicMock()
+            mock_models_instance.generate_content.return_value = mock_response
+            mock_client_instance.models = mock_models_instance
+            mock_genai_class.return_value = mock_client_instance
+
+            client = Client(posthog_client=self.client, api_key="test")
+
+            contents = [
+                {"role": "system", "content": self.test_system_prompt},
+                {"role": "user", "content": self.test_user_message},
+            ]
+
+            client.models.generate_content(
+                model="gemini-2.0-flash",
+                contents=contents,
+                posthog_distinct_id="test-user",
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])
+
+    def test_gemini_system_instruction_parameter(self):
+        """Test Gemini with system_instruction in config parameter."""
+        try:
+            from posthog.ai.gemini import Client
+        except ImportError:
+            self.skipTest("Gemini package not available")
+
+        with patch("google.genai.Client") as mock_genai_class:
+            mock_response = MagicMock()
+            mock_response.candidates = [MagicMock()]
+            mock_response.candidates[0].content.parts = [MagicMock()]
+            mock_response.candidates[0].content.parts[0].text = self.test_response
+            mock_response.usage_metadata.prompt_token_count = 20
+            mock_response.usage_metadata.candidates_token_count = 10
+            mock_response.usage_metadata.cached_content_token_count = None
+            mock_response.usage_metadata.thoughts_token_count = None
+
+            mock_client_instance = MagicMock()
+            mock_models_instance = MagicMock()
+            mock_models_instance.generate_content.return_value = mock_response
+            mock_client_instance.models = mock_models_instance
+            mock_genai_class.return_value = mock_client_instance
+
+            client = Client(posthog_client=self.client, api_key="test")
+
+            contents = [{"role": "user", "content": self.test_user_message}]
+            config = {"system_instruction": self.test_system_prompt}
+
+            client.models.generate_content(
+                model="gemini-2.0-flash",
+                contents=contents,
+                config=config,
+                posthog_distinct_id="test-user",
+            )
+
+            self.assertEqual(len(self.client._enqueue.call_args_list), 1)
+            properties = self.client._enqueue.call_args_list[0][0][0]["properties"]
+            self._assert_system_prompt_captured(properties["$ai_input"])

posthog/test/exception_integrations/__init__.py

@@ -1,3 +0,0 @@
-import pytest
-
-pytest.importorskip("django")

posthog/test/exception_integrations/test_django.py

@@ -1,68 +0,0 @@
-from posthog.exception_integrations.django import DjangoRequestExtractor
-
-DEFAULT_USER_AGENT = (
-    "Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/58.0.3029.110 Safari/537.3"
-)
-
-
-def mock_request_factory(override_headers):
-    class Request:
-        META = {}
-        # TRICKY: Actual django request dict object has case insensitive matching, and strips http from the names
-        headers = {
-            "User-Agent": DEFAULT_USER_AGENT,
-            "Referrer": "http://example.com",
-            "X-Forwarded-For": "193.4.5.12",
-            **(override_headers or {}),
-        }
-
-    return Request()
-
-
-def test_request_extractor_with_no_trace():
-    request = mock_request_factory(None)
-    extractor = DjangoRequestExtractor(request)
-    assert extractor.extract_person_data() == {
-        "ip": "193.4.5.12",
-        "user_agent": DEFAULT_USER_AGENT,
-        "traceparent": None,
-        "distinct_id": None,
-    }
-
-
-def test_request_extractor_with_trace():
-    request = mock_request_factory({"traceparent": "00-0af7651916cd43dd8448eb211c80319c-b7ad6b7169203331-01"})
-    extractor = DjangoRequestExtractor(request)
-    assert extractor.extract_person_data() == {
-        "ip": "193.4.5.12",
-        "user_agent": DEFAULT_USER_AGENT,
-        "traceparent": "00-0af7651916cd43dd8448eb211c80319c-b7ad6b7169203331-01",
-        "distinct_id": None,
-    }
-
-
-def test_request_extractor_with_tracestate():
-    request = mock_request_factory(
-        {
-            "traceparent": "00-0af7651916cd43dd8448eb211c80319c-b7ad6b7169203331-01",
-            "tracestate": "posthog-distinct-id=1234",
-        }
-    )
-    extractor = DjangoRequestExtractor(request)
-    assert extractor.extract_person_data() == {
-        "ip": "193.4.5.12",
-        "user_agent": DEFAULT_USER_AGENT,
-        "traceparent": "00-0af7651916cd43dd8448eb211c80319c-b7ad6b7169203331-01",
-        "distinct_id": "1234",
-    }
-
-
-def test_request_extractor_with_complicated_tracestate():
-    request = mock_request_factory({"tracestate": "posthog-distinct-id=alohaMountainsXUYZ,rojo=00f067aa0ba902b7"})
-    extractor = DjangoRequestExtractor(request)
-    assert extractor.extract_person_data() == {
-        "ip": "193.4.5.12",
-        "user_agent": DEFAULT_USER_AGENT,
-        "traceparent": None,
-        "distinct_id": "alohaMountainsXUYZ",
-    }

posthog/test/integrations/test_middleware.py

@@ -0,0 +1,773 @@
+from posthog.contexts import (
+    new_context,
+    get_context_session_id,
+    get_context_distinct_id,
+)
+import unittest
+from unittest.mock import Mock, patch
+import asyncio
+
+# Configure Django settings before importing middleware
+import django
+from django.conf import settings
+
+if not settings.configured:
+    settings.configure(
+        DEBUG=True,
+        SECRET_KEY="test-secret-key",
+        INSTALLED_APPS=[],
+        MIDDLEWARE=[],
+    )
+    django.setup()
+
+from posthog.integrations.django import PosthogContextMiddleware
+
+
+class MockRequest:
+    """Mock Django HttpRequest object"""
+
+    def __init__(
+        self,
+        headers=None,
+        method="GET",
+        path="/test",
+        host="example.com",
+        is_secure=False,
+    ):
+        self.headers = headers or {}
+        self.method = method
+        self.path = path
+        self._host = host
+        self._is_secure = is_secure
+
+    def build_absolute_uri(self):
+        scheme = "https" if self._is_secure else "http"
+        return f"{scheme}://{self._host}{self.path}"
+
+
+class TestPosthogContextMiddleware(unittest.TestCase):
+    def create_middleware(
+        self,
+        extra_tags=None,
+        request_filter=None,
+        tag_map=None,
+        capture_exceptions=True,
+        get_response=None,
+    ):
+        """Helper to create middleware instance with mock Django settings"""
+        if get_response is None:
+            get_response = Mock()
+
+        with patch("django.conf.settings") as mock_settings:
+            # Configure mock settings
+            mock_settings.POSTHOG_MW_EXTRA_TAGS = extra_tags
+            mock_settings.POSTHOG_MW_REQUEST_FILTER = request_filter
+            mock_settings.POSTHOG_MW_TAG_MAP = tag_map
+            mock_settings.POSTHOG_MW_CAPTURE_EXCEPTIONS = capture_exceptions
+            mock_settings.POSTHOG_MW_CLIENT = None
+
+            # Make hasattr work correctly
+            def mock_hasattr(obj, name):
+                return name in [
+                    "POSTHOG_MW_EXTRA_TAGS",
+                    "POSTHOG_MW_REQUEST_FILTER",
+                    "POSTHOG_MW_TAG_MAP",
+                    "POSTHOG_MW_CAPTURE_EXCEPTIONS",
+                    "POSTHOG_MW_CLIENT",
+                ]
+
+            with patch("builtins.hasattr", side_effect=mock_hasattr):
+                middleware = PosthogContextMiddleware(get_response)
+
+        return middleware
+
+    def test_extract_tags_basic(self):
+        with new_context():
+            """Test basic tag extraction from request"""
+            middleware = self.create_middleware()
+            request = MockRequest(
+                headers={
+                    "X-POSTHOG-SESSION-ID": "session-123",
+                    "X-POSTHOG-DISTINCT-ID": "user-456",
+                },
+                method="POST",
+                path="/api/test",
+                host="example.com",
+                is_secure=True,
+            )
+
+            tags = middleware.extract_tags(request)
+
+            self.assertEqual(get_context_session_id(), "session-123")
+            self.assertEqual(get_context_distinct_id(), "user-456")
+            self.assertEqual(tags["$current_url"], "https://example.com/api/test")
+            self.assertEqual(tags["$request_method"], "POST")
+
+    def test_extract_tags_missing_headers(self):
+        """Test tag extraction when PostHog headers are missing"""
+
+        with new_context():
+            middleware = self.create_middleware()
+            request = MockRequest(headers={}, method="GET", path="/home")
+
+            tags = middleware.extract_tags(request)
+
+            self.assertIsNone(get_context_session_id())
+            self.assertIsNone(get_context_distinct_id())
+            self.assertEqual(tags["$current_url"], "http://example.com/home")
+            self.assertEqual(tags["$request_method"], "GET")
+
+    def test_extract_tags_partial_headers(self):
+        """Test tag extraction with only some PostHog headers present"""
+
+        with new_context():
+            middleware = self.create_middleware()
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "session-only"}, method="PUT"
+            )
+
+            tags = middleware.extract_tags(request)
+
+            self.assertEqual(get_context_session_id(), "session-only")
+            self.assertIsNone(get_context_distinct_id())
+            self.assertEqual(tags["$request_method"], "PUT")
+
+    def test_extract_tags_with_extra_tags(self):
+        """Test tag extraction with extra_tags function"""
+
+        def extra_tags_func(request):
+            return {"custom_tag": "custom_value", "user_id": "789"}
+
+        with new_context():
+            middleware = self.create_middleware(extra_tags=extra_tags_func)
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "session-123"}, method="GET"
+            )
+
+            tags = middleware.extract_tags(request)
+
+            self.assertEqual(get_context_session_id(), "session-123")
+            self.assertEqual(tags["custom_tag"], "custom_value")
+            self.assertEqual(tags["user_id"], "789")
+
+    def test_extract_tags_with_tag_map(self):
+        """Test tag extraction with tag_map function"""
+
+        def extra_tags_func(request):
+            return {"custom_tag": "custom_value", "user_id": "789"}
+
+        def tag_map_func(tags):
+            if "custom_tag" in tags:
+                tags["mapped_custom_tag"] = f"mapped_{tags['custom_tag']}"
+                del tags["custom_tag"]
+            return tags
+
+        with new_context():
+            middleware = self.create_middleware(
+                tag_map=tag_map_func, extra_tags=extra_tags_func
+            )
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "session-123"}, method="GET"
+            )
+
+            tags = middleware.extract_tags(request)
+
+            self.assertEqual(tags["mapped_custom_tag"], "mapped_custom_value")
+
+    def test_extract_tags_extra_tags_returns_none(self):
+        """Test tag extraction when extra_tags returns None"""
+
+        def extra_tags_func(request):
+            return None
+
+        middleware = self.create_middleware(extra_tags=extra_tags_func)
+        request = MockRequest(method="GET")
+
+        tags = middleware.extract_tags(request)
+
+        self.assertEqual(tags["$request_method"], "GET")
+        # Should not crash when extra_tags returns None
+
+    def test_extract_tags_extra_tags_returns_empty_dict(self):
+        """Test tag extraction when extra_tags returns empty dict"""
+
+        def extra_tags_func(request):
+            return {}
+
+        middleware = self.create_middleware(extra_tags=extra_tags_func)
+        request = MockRequest(method="PATCH")
+
+        tags = middleware.extract_tags(request)
+
+        self.assertEqual(tags["$request_method"], "PATCH")
+
+    def test_process_exception_called_during_view_exception(self):
+        """
+        Unit test verifying process_exception captures exceptions per Django's contract.
+
+        Since this is a library test (no Django runtime), we simulate how Django
+        would invoke our middleware in production:
+        1. Middleware.__call__ creates context with request tags
+        2. View raises exception inside get_response
+        3. Django's BaseHandler catches it, calls process_exception, returns error response
+        4. Exception never propagates to middleware's context manager
+
+        We manually call process_exception to simulate Django's behavior - this is
+        the only way to test the hook without a full Django integration test.
+        """
+        mock_client = Mock()
+        view_exception = ValueError("View raised this error")
+        error_response = Mock(status_code=500)
+
+        def mock_get_response(request):
+            # Simulate Django's exception handling: catches view exception,
+            # calls process_exception hook if it exists, returns error response
+            if hasattr(middleware, "process_exception"):
+                middleware.process_exception(request, view_exception)
+            return error_response
+
+        middleware = self.create_middleware(get_response=mock_get_response)
+        middleware.client = mock_client
+
+        request = MockRequest(
+            headers={"X-POSTHOG-DISTINCT-ID": "test-user"},
+            method="POST",
+            path="/api/endpoint",
+        )
+        response = middleware(request)
+
+        self.assertEqual(response.status_code, 500)
+        mock_client.capture_exception.assert_called_once_with(view_exception)
+
+    def test_process_exception_respects_capture_exceptions_false(self):
+        """Verify process_exception respects capture_exceptions=False setting"""
+        mock_client = Mock()
+        view_exception = ValueError("Should not be captured")
+
+        def mock_get_response(request):
+            if hasattr(middleware, "process_exception"):
+                middleware.process_exception(request, view_exception)
+            return Mock(status_code=500)
+
+        middleware = self.create_middleware(
+            capture_exceptions=False, get_response=mock_get_response
+        )
+        middleware.client = mock_client
+
+        request = MockRequest()
+        middleware(request)
+
+        mock_client.capture_exception.assert_not_called()
+
+    def test_process_exception_respects_request_filter(self):
+        """Verify process_exception respects request_filter setting"""
+        mock_client = Mock()
+        view_exception = ValueError("Should be filtered")
+
+        def mock_get_response(request):
+            if hasattr(middleware, "process_exception"):
+                middleware.process_exception(request, view_exception)
+            return Mock(status_code=500)
+
+        middleware = self.create_middleware(
+            request_filter=lambda req: False,
+            capture_exceptions=True,
+            get_response=mock_get_response,
+        )
+        middleware.client = mock_client
+
+        request = MockRequest()
+        middleware(request)
+
+        mock_client.capture_exception.assert_not_called()
+
+
+class TestPosthogContextMiddlewareSync(unittest.TestCase):
+    """Test synchronous middleware behavior"""
+
+    def test_sync_middleware_call(self):
+        """Test that sync middleware correctly processes requests"""
+        mock_response = Mock()
+        get_response = Mock(return_value=mock_response)
+
+        # Create middleware with sync get_response
+        middleware = PosthogContextMiddleware(get_response)
+
+        # Verify sync mode detected
+        self.assertFalse(middleware._is_coroutine)
+
+        request = MockRequest(
+            headers={"X-POSTHOG-SESSION-ID": "test-session"},
+            method="GET",
+            path="/test",
+        )
+
+        with new_context():
+            response = middleware(request)
+
+            # Verify response returned
+            self.assertEqual(response, mock_response)
+            get_response.assert_called_once_with(request)
+
+    def test_sync_middleware_with_filter(self):
+        """Test sync middleware respects request filter"""
+        mock_response = Mock()
+        get_response = Mock(return_value=mock_response)
+
+        # Create middleware with request filter that filters all requests
+        def request_filter(req):
+            return False
+
+        middleware = PosthogContextMiddleware.__new__(PosthogContextMiddleware)
+        middleware.get_response = get_response
+        middleware._is_coroutine = False
+        middleware.request_filter = request_filter
+        middleware.capture_exceptions = True
+        middleware.client = None
+
+        request = MockRequest()
+
+        # Should skip context creation and return response directly
+        response = middleware(request)
+        self.assertEqual(response, mock_response)
+        get_response.assert_called_once_with(request)
+
+    def test_view_exceptions_only_captured_via_process_exception(self):
+        """
+        Demonstrates that process_exception is required to capture view exceptions.
+
+        In production Django, view exceptions don't propagate to middleware's context
+        manager because Django's BaseHandler catches them first and converts them to
+        error responses. Django provides the exception via process_exception hook instead.
+
+        This unit test proves:
+        1. Context manager in __call__ never sees view exceptions (Django intercepts)
+        2. Only process_exception can capture them
+        3. Without process_exception, exceptions are silently lost (v6.7.5 regression)
+
+        We manually call process_exception to verify the hook works - in production,
+        Django's BaseHandler would call it when a view raises.
+        """
+        mock_client = Mock()
+        get_response = Mock(return_value=Mock(status_code=500))
+
+        middleware = PosthogContextMiddleware(get_response)
+        middleware.client = mock_client
+
+        def get_response_simulating_django(request):
+            # Simulates Django behavior: view exception converted to error response,
+            # never propagates to middleware's context manager
+            return Mock(status_code=500)
+
+        middleware._sync_get_response = get_response_simulating_django
+
+        request = MockRequest()
+
+        response = middleware(request)
+        self.assertEqual(response.status_code, 500)
+
+        # Context manager didn't capture anything - exception was intercepted by Django
+        mock_client.capture_exception.assert_not_called()
+
+        # Verify process_exception hook exists and captures exceptions when called
+        if hasattr(middleware, "process_exception"):
+            exception = ValueError("View error")
+            middleware.process_exception(request, exception)
+            mock_client.capture_exception.assert_called_once_with(exception)
+        else:
+            self.fail(
+                "process_exception missing - view exceptions will not be captured!"
+            )
+
+
+class TestPosthogContextMiddlewareAsync(unittest.TestCase):
+    """Test asynchronous middleware behavior"""
+
+    def test_async_middleware_detection(self):
+        """Test that async get_response is correctly detected"""
+
+        async def async_get_response(request):
+            return Mock()
+
+        middleware = PosthogContextMiddleware(async_get_response)
+
+        # Verify async mode detected
+        self.assertTrue(middleware._is_coroutine)
+
+    def test_async_middleware_call(self):
+        """Test that async middleware correctly processes requests"""
+
+        async def run_test():
+            mock_response = Mock()
+
+            async def async_get_response(request):
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "async-session"},
+                method="POST",
+                path="/async-test",
+            )
+
+            with new_context():
+                # Call should return the coroutine from __acall__
+                result = middleware(request)
+
+                # Verify it's a coroutine
+                self.assertTrue(asyncio.iscoroutine(result))
+
+                # Await the result
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_with_filter(self):
+        """Test async middleware respects request filter"""
+
+        async def run_test():
+            mock_response = Mock()
+
+            async def async_get_response(request):
+                return mock_response
+
+            # Properly initialize middleware
+            middleware = PosthogContextMiddleware(async_get_response)
+            # Override request filter after initialization
+            middleware.request_filter = lambda req: False
+
+            request = MockRequest()
+
+            # Should skip context creation and return response directly
+            result = middleware(request)
+            response = await result
+            self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_context_propagation(self):
+        """Test that async middleware properly propagates context"""
+
+        async def run_test():
+            mock_response = Mock()
+
+            async def async_get_response(request):
+                # Verify context is available during async processing
+                session_id = get_context_session_id()
+                self.assertEqual(session_id, "async-session-123")
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "async-session-123"},
+                method="GET",
+            )
+
+            with new_context():
+                result = middleware(request)
+                await result
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_exception_capture(self):
+        """Test that async middleware captures exceptions during request processing"""
+
+        async def run_test():
+            mock_client = Mock()
+
+            # Make async_get_response raise an exception
+            async def raise_exception(request):
+                raise ValueError("Async test exception")
+
+            # Properly initialize middleware
+            middleware = PosthogContextMiddleware(raise_exception)
+            middleware.client = mock_client  # Override with mock client
+
+            request = MockRequest()
+
+            # Should capture exception and re-raise
+            with self.assertRaises(ValueError):
+                result = middleware(request)
+                await result
+
+            # Verify exception was captured by middleware
+            mock_client.capture_exception.assert_called_once()
+            captured_exception = mock_client.capture_exception.call_args[0][0]
+            self.assertIsInstance(captured_exception, ValueError)
+            self.assertEqual(str(captured_exception), "Async test exception")
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_with_authenticated_user(self):
+        """
+        Test that async middleware correctly extracts user info in async context.
+
+        Django's request.user is a SimpleLazyObject that defers DB access.
+        In async context, accessing it directly raises SynchronousOnlyOperation.
+        The middleware should use request.auser() instead.
+
+        This tests the fix for issue #355.
+        """
+
+        async def run_test():
+            mock_response = Mock()
+            mock_user = Mock()
+            mock_user.is_authenticated = True
+            mock_user.pk = 123
+            mock_user.email = "test@example.com"
+
+            async def async_get_response(request):
+                # Verify user info was extracted and set as distinct_id
+                distinct_id = get_context_distinct_id()
+                self.assertEqual(distinct_id, "123")
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.client = Mock()
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "test-session"}, method="GET"
+            )
+
+            # Mock auser() to return authenticated user
+            async def mock_auser():
+                return mock_user
+
+            request.auser = mock_auser
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_with_unauthenticated_user(self):
+        """
+        Test that async middleware handles unauthenticated users correctly.
+        """
+
+        async def run_test():
+            mock_response = Mock()
+            mock_user = Mock()
+            mock_user.is_authenticated = False  # Not authenticated
+
+            async def async_get_response(request):
+                # Verify no distinct_id was set (no user)
+                distinct_id = get_context_distinct_id()
+                self.assertIsNone(distinct_id)
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.client = Mock()
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "test-session"}, method="GET"
+            )
+
+            async def mock_auser():
+                return mock_user
+
+            request.auser = mock_auser
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_without_user_attribute(self):
+        """
+        Test that async middleware handles requests without user attribute (no auth middleware).
+        """
+
+        async def run_test():
+            mock_response = Mock()
+
+            async def async_get_response(request):
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.client = Mock()
+
+            # Request without auser method (no auth middleware)
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "test-session"}, method="GET"
+            )
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_with_extra_tags(self):
+        """
+        Test that async middleware works with extra_tags callback.
+        """
+
+        async def run_test():
+            mock_response = Mock()
+
+            def extra_tags_callback(request):
+                # Simple sync callback - should work
+                return {"custom_tag": "custom_value"}
+
+            async def async_get_response(request):
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.extra_tags = extra_tags_callback
+            middleware.client = Mock()
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "test-session"}, method="GET"
+            )
+
+            # Mock auser for no user
+            async def mock_auser():
+                return None
+
+            request.auser = mock_auser
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_with_tag_map(self):
+        """
+        Test that async middleware works with tag_map callback.
+        """
+
+        async def run_test():
+            mock_response = Mock()
+
+            def tag_map_callback(tags):
+                # Simple sync callback - should work
+                tags["mapped"] = "yes"
+                return tags
+
+            async def async_get_response(request):
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.tag_map = tag_map_callback
+            middleware.client = Mock()
+
+            request = MockRequest(
+                headers={"X-POSTHOG-SESSION-ID": "test-session"}, method="GET"
+            )
+
+            # Mock auser for no user
+            async def mock_auser():
+                return None
+
+            request.auser = mock_auser
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+    def test_async_middleware_user_extraction_with_all_headers(self):
+        """
+        Test async middleware extracts all request info correctly.
+        """
+
+        async def run_test():
+            mock_response = Mock()
+            mock_user = Mock()
+            mock_user.is_authenticated = True
+            mock_user.pk = 456
+            mock_user.email = "async@test.com"
+
+            async def async_get_response(request):
+                # Verify all context was set correctly
+                distinct_id = get_context_distinct_id()
+                session_id = get_context_session_id()
+                self.assertEqual(distinct_id, "456")
+                self.assertEqual(session_id, "async-sess-123")
+                return mock_response
+
+            middleware = PosthogContextMiddleware(async_get_response)
+            middleware.client = Mock()
+
+            request = MockRequest(
+                headers={
+                    "X-POSTHOG-SESSION-ID": "async-sess-123",
+                    "X-Forwarded-For": "192.168.1.1",
+                    "User-Agent": "TestAgent/1.0",
+                },
+                method="POST",
+                path="/api/test",
+            )
+
+            async def mock_auser():
+                return mock_user
+
+            request.auser = mock_auser
+
+            with new_context():
+                result = middleware(request)
+                response = await result
+                self.assertEqual(response, mock_response)
+
+        asyncio.run(run_test())
+
+
+class TestPosthogContextMiddlewareHybrid(unittest.TestCase):
+    """Test hybrid middleware behavior with mixed sync/async chains"""
+
+    def test_hybrid_flags_set(self):
+        """Test that both capability flags are set"""
+        self.assertTrue(PosthogContextMiddleware.sync_capable)
+        self.assertTrue(PosthogContextMiddleware.async_capable)
+
+    def test_sync_to_async_routing(self):
+        """Test that __call__ routes to __acall__ when async"""
+
+        async def run_test():
+            async def async_get_response(request):
+                return Mock()
+
+            middleware = PosthogContextMiddleware(async_get_response)
+
+            # Verify routing happens
+            request = MockRequest()
+            result = middleware(request)
+
+            # Should be a coroutine from __acall__
+            self.assertTrue(asyncio.iscoroutine(result))
+            await result  # Clean up
+
+        asyncio.run(run_test())
+
+    def test_sync_path_direct_return(self):
+        """Test that sync path returns directly without coroutine"""
+        mock_response = Mock()
+
+        def sync_get_response(request):
+            return mock_response
+
+        middleware = PosthogContextMiddleware(sync_get_response)
+
+        request = MockRequest()
+        result = middleware(request)
+
+        # Should NOT be a coroutine
+        self.assertFalse(asyncio.iscoroutine(result))
+        self.assertEqual(result, mock_response)
+
+
+if __name__ == "__main__":
+    unittest.main()

posthog/test/test_before_send.py

@@ -0,0 +1,218 @@
+import unittest
+
+import mock
+
+from posthog.client import Client
+from posthog.test.test_utils import FAKE_TEST_API_KEY
+
+
+class TestClient(unittest.TestCase):
+    @classmethod
+    def setUpClass(cls):
+        # This ensures no real HTTP POST requests are made
+        cls.client_post_patcher = mock.patch("posthog.client.batch_post")
+        cls.consumer_post_patcher = mock.patch("posthog.consumer.batch_post")
+        cls.client_post_patcher.start()
+        cls.consumer_post_patcher.start()
+
+    @classmethod
+    def tearDownClass(cls):
+        cls.client_post_patcher.stop()
+        cls.consumer_post_patcher.stop()
+
+    def set_fail(self, e, batch):
+        """Mark the failure handler"""
+        print("FAIL", e, batch)  # noqa: T201
+        self.failed = True
+
+    def setUp(self):
+        self.failed = False
+        self.client = Client(FAKE_TEST_API_KEY, on_error=self.set_fail)
+
+    def test_before_send_callback_modifies_event(self):
+        """Test that before_send callback can modify events."""
+        processed_events = []
+
+        def my_before_send(event):
+            processed_events.append(event.copy())
+            if "properties" not in event:
+                event["properties"] = {}
+            event["properties"]["processed_by_before_send"] = True
+            return event
+
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=my_before_send,
+                sync_mode=True,
+            )
+            msg_uuid = client.capture(
+                "test_event", distinct_id="user1", properties={"original": "value"}
+            )
+
+            self.assertIsNotNone(msg_uuid)
+
+            # Get the enqueued message from the mock
+            mock_post.assert_called_once()
+            batch_data = mock_post.call_args[1]["batch"]
+            enqueued_msg = batch_data[0]
+
+            self.assertEqual(
+                enqueued_msg["properties"]["processed_by_before_send"], True
+            )
+            self.assertEqual(enqueued_msg["properties"]["original"], "value")
+            self.assertEqual(len(processed_events), 1)
+            self.assertEqual(processed_events[0]["event"], "test_event")
+
+    def test_before_send_callback_drops_event(self):
+        """Test that before_send callback can drop events by returning None."""
+
+        def drop_test_events(event):
+            if event.get("event") == "test_drop_me":
+                return None
+            return event
+
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=drop_test_events,
+                sync_mode=True,
+            )
+
+            # Event should be dropped
+            msg_uuid = client.capture("test_drop_me", distinct_id="user1")
+            self.assertIsNone(msg_uuid)
+
+            # Event should go through
+            msg_uuid = client.capture("keep_me", distinct_id="user1")
+            self.assertIsNotNone(msg_uuid)
+
+            # Check the enqueued message
+            mock_post.assert_called_once()
+            batch_data = mock_post.call_args[1]["batch"]
+            enqueued_msg = batch_data[0]
+            self.assertEqual(enqueued_msg["event"], "keep_me")
+
+    def test_before_send_callback_handles_exceptions(self):
+        """Test that exceptions in before_send don't crash the client."""
+
+        def buggy_before_send(event):
+            raise ValueError("Oops!")
+
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=buggy_before_send,
+                sync_mode=True,
+            )
+            msg_uuid = client.capture("robust_event", distinct_id="user1")
+
+            # Event should still be sent despite the exception
+            self.assertIsNotNone(msg_uuid)
+
+            # Check the enqueued message
+            mock_post.assert_called_once()
+            batch_data = mock_post.call_args[1]["batch"]
+            enqueued_msg = batch_data[0]
+            self.assertEqual(enqueued_msg["event"], "robust_event")
+
+    def test_before_send_callback_works_with_all_event_types(self):
+        """Test that before_send works with capture, set, etc."""
+
+        def add_marker(event):
+            if "properties" not in event:
+                event["properties"] = {}
+            event["properties"]["marked"] = True
+            return event
+
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=add_marker,
+                sync_mode=True,
+            )
+
+            # Test capture
+            msg_uuid = client.capture("event", distinct_id="user1")
+            self.assertIsNotNone(msg_uuid)
+
+            # Test set
+            msg_uuid = client.set(distinct_id="user1", properties={"prop": "value"})
+            self.assertIsNotNone(msg_uuid)
+
+            # Check all events were marked
+            self.assertEqual(mock_post.call_count, 2)
+            for call in mock_post.call_args_list:
+                batch_data = call[1]["batch"]
+                enqueued_msg = batch_data[0]
+                self.assertTrue(enqueued_msg["properties"]["marked"])
+
+    def test_before_send_callback_disabled_when_none(self):
+        """Test that client works normally when before_send is None."""
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=None,
+                sync_mode=True,
+            )
+            msg_uuid = client.capture("normal_event", distinct_id="user1")
+            self.assertIsNotNone(msg_uuid)
+
+            # Check the event was sent normally
+            mock_post.assert_called_once()
+            batch_data = mock_post.call_args[1]["batch"]
+            enqueued_msg = batch_data[0]
+            self.assertEqual(enqueued_msg["event"], "normal_event")
+
+    def test_before_send_callback_pii_scrubbing_example(self):
+        """Test a realistic PII scrubbing use case."""
+
+        def scrub_pii(event):
+            properties = event.get("properties", {})
+
+            # Mask email but keep domain
+            if "email" in properties:
+                email = properties["email"]
+                if "@" in email:
+                    domain = email.split("@")[1]
+                    properties["email"] = f"***@{domain}"
+                else:
+                    properties["email"] = "***"
+
+            # Remove credit card
+            properties.pop("credit_card", None)
+
+            return event
+
+        with mock.patch("posthog.client.batch_post") as mock_post:
+            client = Client(
+                FAKE_TEST_API_KEY,
+                on_error=self.set_fail,
+                before_send=scrub_pii,
+                sync_mode=True,
+            )
+            msg_uuid = client.capture(
+                "form_submit",
+                distinct_id="user1",
+                properties={
+                    "email": "user@example.com",
+                    "credit_card": "1234-5678-9012-3456",
+                    "form_name": "contact",
+                },
+            )
+
+            self.assertIsNotNone(msg_uuid)
+
+            # Check the enqueued message was scrubbed
+            mock_post.assert_called_once()
+            batch_data = mock_post.call_args[1]["batch"]
+            enqueued_msg = batch_data[0]
+
+            self.assertEqual(enqueued_msg["properties"]["email"], "***@example.com")
+            self.assertNotIn("credit_card", enqueued_msg["properties"])
+            self.assertEqual(enqueued_msg["properties"]["form_name"], "contact")

posthog/test/test_consumer.py

@@ -1,8 +1,10 @@
 import json
 import time
 import unittest
+from typing import Any
 
 import mock
+from parameterized import parameterized
 
 try:
     from queue import Queue
@@ -14,15 +16,19 @@ from posthog.request import APIError
 from posthog.test.test_utils import TEST_API_KEY
 
 
+def _track_event(event_name: str = "python event") -> dict[str, str]:
+    return {"type": "track", "event": event_name, "distinct_id": "distinct_id"}
+
+
 class TestConsumer(unittest.TestCase):
-    def test_next(self):
+    def test_next(self) -> None:
         q = Queue()
         consumer = Consumer(q, "")
         q.put(1)
         next = consumer.next()
         self.assertEqual(next, [1])
 
-    def test_next_limit(self):
+    def test_next_limit(self) -> None:
         q = Queue()
         flush_at = 50
         consumer = Consumer(q, "", flush_at)
@@ -31,7 +37,7 @@ class TestConsumer(unittest.TestCase):
         next = consumer.next()
         self.assertEqual(next, list(range(flush_at)))
 
-    def test_dropping_oversize_msg(self):
+    def test_dropping_oversize_msg(self) -> None:
         q = Queue()
         consumer = Consumer(q, "")
         oversize_msg = {"m": "x" * MAX_MSG_SIZE}
@@ -40,15 +46,14 @@ class TestConsumer(unittest.TestCase):
         self.assertEqual(next, [])
         self.assertTrue(q.empty())
 
-    def test_upload(self):
+    def test_upload(self) -> None:
         q = Queue()
         consumer = Consumer(q, TEST_API_KEY)
-        track = {"type": "track", "event": "python event", "distinct_id": "distinct_id"}
-        q.put(track)
+        q.put(_track_event())
         success = consumer.upload()
         self.assertTrue(success)
 
-    def test_flush_interval(self):
+    def test_flush_interval(self) -> None:
         # Put _n_ items in the queue, pausing a little bit more than
         # _flush_interval_ after each one.
         # The consumer should upload _n_ times.
@@ -57,113 +62,138 @@ class TestConsumer(unittest.TestCase):
         consumer = Consumer(q, TEST_API_KEY, flush_at=10, flush_interval=flush_interval)
         with mock.patch("posthog.consumer.batch_post") as mock_post:
             consumer.start()
-            for i in range(0, 3):
-                track = {"type": "track", "event": "python event %d" % i, "distinct_id": "distinct_id"}
-                q.put(track)
+            for i in range(3):
+                q.put(_track_event("python event %d" % i))
                 time.sleep(flush_interval * 1.1)
             self.assertEqual(mock_post.call_count, 3)
 
-    def test_multiple_uploads_per_interval(self):
+    def test_multiple_uploads_per_interval(self) -> None:
         # Put _flush_at*2_ items in the queue at once, then pause for
         # _flush_interval_. The consumer should upload 2 times.
         q = Queue()
         flush_interval = 0.5
         flush_at = 10
-        consumer = Consumer(q, TEST_API_KEY, flush_at=flush_at, flush_interval=flush_interval)
+        consumer = Consumer(
+            q, TEST_API_KEY, flush_at=flush_at, flush_interval=flush_interval
+        )
         with mock.patch("posthog.consumer.batch_post") as mock_post:
             consumer.start()
-            for i in range(0, flush_at * 2):
-                track = {"type": "track", "event": "python event %d" % i, "distinct_id": "distinct_id"}
-                q.put(track)
+            for i in range(flush_at * 2):
+                q.put(_track_event("python event %d" % i))
             time.sleep(flush_interval * 1.1)
             self.assertEqual(mock_post.call_count, 2)
 
-    def test_request(self):
+    def test_request(self) -> None:
         consumer = Consumer(None, TEST_API_KEY)
-        track = {"type": "track", "event": "python event", "distinct_id": "distinct_id"}
-        consumer.request([track])
+        consumer.request([_track_event()])
 
-    def _test_request_retry(self, consumer, expected_exception, exception_count):
-        def mock_post(*args, **kwargs):
-            mock_post.call_count += 1
-            if mock_post.call_count <= exception_count:
-                raise expected_exception
+    def _run_retry_test(
+        self, exception: Exception, exception_count: int, retries: int = 10
+    ) -> None:
+        call_count = [0]
 
-        mock_post.call_count = 0
+        def mock_post(*args: Any, **kwargs: Any) -> None:
+            call_count[0] += 1
+            if call_count[0] <= exception_count:
+                raise exception
 
-        with mock.patch("posthog.consumer.batch_post", mock.Mock(side_effect=mock_post)):
-            track = {"type": "track", "event": "python event", "distinct_id": "distinct_id"}
-            # request() should succeed if the number of exceptions raised is
-            # less than the retries paramater.
-            if exception_count <= consumer.retries:
-                consumer.request([track])
+        consumer = Consumer(None, TEST_API_KEY, retries=retries)
+        with mock.patch(
+            "posthog.consumer.batch_post", mock.Mock(side_effect=mock_post)
+        ):
+            if exception_count <= retries:
+                consumer.request([_track_event()])
             else:
-                # if exceptions are raised more times than the retries
-                # parameter, we expect the exception to be returned to
-                # the caller.
-                try:
-                    consumer.request([track])
-                except type(expected_exception) as exc:
-                    self.assertEqual(exc, expected_exception)
-                else:
-                    self.fail(
-                        "request() should raise an exception if still failing after %d retries" % consumer.retries
-                    )
+                with self.assertRaises(type(exception)):
+                    consumer.request([_track_event()])
 
-    def test_request_retry(self):
-        # we should retry on general errors
-        consumer = Consumer(None, TEST_API_KEY)
-        self._test_request_retry(consumer, Exception("generic exception"), 2)
+    @parameterized.expand(
+        [
+            ("general_errors", Exception("generic exception"), 2),
+            ("server_errors", APIError(500, "Internal Server Error"), 2),
+            ("rate_limit_errors", APIError(429, "Too Many Requests"), 2),
+        ]
+    )
+    def test_request_retries_on_retriable_errors(
+        self, _name: str, exception: Exception, exception_count: int
+    ) -> None:
+        self._run_retry_test(exception, exception_count)
 
-        # we should retry on server errors
-        consumer = Consumer(None, TEST_API_KEY)
-        self._test_request_retry(consumer, APIError(500, "Internal Server Error"), 2)
+    def test_request_does_not_retry_client_errors(self) -> None:
+        with self.assertRaises(APIError):
+            self._run_retry_test(APIError(400, "Client Errors"), 1)
 
-        # we should retry on HTTP 429 errors
-        consumer = Consumer(None, TEST_API_KEY)
-        self._test_request_retry(consumer, APIError(429, "Too Many Requests"), 2)
+    def test_request_fails_when_exceptions_exceed_retries(self) -> None:
+        self._run_retry_test(APIError(500, "Internal Server Error"), 4, retries=3)
 
-        # we should NOT retry on other client errors
-        consumer = Consumer(None, TEST_API_KEY)
-        api_error = APIError(400, "Client Errors")
-        try:
-            self._test_request_retry(consumer, api_error, 1)
-        except APIError:
-            pass
-        else:
-            self.fail("request() should not retry on client errors")
-
-        # test for number of exceptions raise > retries value
-        consumer = Consumer(None, TEST_API_KEY, retries=3)
-        self._test_request_retry(consumer, APIError(500, "Internal Server Error"), 3)
-
-    def test_pause(self):
+    def test_pause(self) -> None:
         consumer = Consumer(None, TEST_API_KEY)
         consumer.pause()
         self.assertFalse(consumer.running)
 
-    def test_max_batch_size(self):
+    def test_max_batch_size(self) -> None:
         q = Queue()
         consumer = Consumer(q, TEST_API_KEY, flush_at=100000, flush_interval=3)
         properties = {}
         for n in range(0, 500):
             properties[str(n)] = "one_long_property_value_to_build_a_big_event"
-        track = {"type": "track", "event": "python event", "distinct_id": "distinct_id", "properties": properties}
+        track = {
+            "type": "track",
+            "event": "python event",
+            "distinct_id": "distinct_id",
+            "properties": properties,
+        }
         msg_size = len(json.dumps(track).encode())
         # Let's capture 8MB of data to trigger two batches
         n_msgs = int(8_000_000 / msg_size)
 
-        def mock_post_fn(_, data, **kwargs):
+        def mock_post_fn(_: str, data: str, **kwargs: Any) -> mock.Mock:
             res = mock.Mock()
             res.status_code = 200
             request_size = len(data.encode())
             # Batches close after the first message bringing it bigger than BATCH_SIZE_LIMIT, let's add 10% of margin
-            self.assertTrue(request_size < (5 * 1024 * 1024) * 1.1, "batch size (%d) higher than limit" % request_size)
+            self.assertTrue(
+                request_size < (5 * 1024 * 1024) * 1.1,
+                "batch size (%d) higher than limit" % request_size,
+            )
             return res
 
-        with mock.patch("posthog.request._session.post", side_effect=mock_post_fn) as mock_post:
+        with mock.patch(
+            "posthog.request._session.post", side_effect=mock_post_fn
+        ) as mock_post:
             consumer.start()
             for _ in range(0, n_msgs + 2):
                 q.put(track)
             q.join()
             self.assertEqual(mock_post.call_count, 2)
+
+    @parameterized.expand(
+        [
+            ("on_error_succeeds", False),
+            ("on_error_raises", True),
+        ]
+    )
+    def test_upload_exception_calls_on_error_and_does_not_raise(
+        self, _name: str, on_error_raises: bool
+    ) -> None:
+        on_error_called: list[tuple[Exception, list[dict[str, str]]]] = []
+
+        def on_error(e: Exception, batch: list[dict[str, str]]) -> None:
+            on_error_called.append((e, batch))
+            if on_error_raises:
+                raise Exception("on_error failed")
+
+        q = Queue()
+        consumer = Consumer(q, TEST_API_KEY, on_error=on_error)
+        track = _track_event()
+        q.put(track)
+
+        with mock.patch.object(
+            consumer, "request", side_effect=Exception("request failed")
+        ):
+            result = consumer.upload()
+
+        self.assertFalse(result)
+        self.assertEqual(len(on_error_called), 1)
+        self.assertEqual(str(on_error_called[0][0]), "request failed")
+        self.assertEqual(on_error_called[0][1], [track])

posthog/test/test_contexts.py

@@ -0,0 +1,233 @@
+import unittest
+from unittest.mock import patch
+
+from posthog.contexts import (
+    get_tags,
+    new_context,
+    scoped,
+    tag,
+    identify_context,
+    set_context_session,
+    get_context_session_id,
+    get_context_distinct_id,
+)
+
+
+class TestContexts(unittest.TestCase):
+    def test_tag_and_get_tags(self):
+        with new_context(fresh=True):
+            tag("key1", "value1")
+            tag("key2", 2)
+
+            tags = get_tags()
+            assert tags["key1"] == "value1"
+            assert tags["key2"] == 2
+
+    def test_new_context_isolation(self):
+        with new_context(fresh=True):
+            # Set tag in outer context
+            tag("outer", "value")
+
+            with new_context(fresh=True):
+                # Inner context should start empty
+                assert get_tags() == {}
+
+                # Set tag in inner context
+                tag("inner", "value")
+                assert get_tags()["inner"] == "value"
+
+                # Outer tag should not be visible
+                self.assertNotIn("outer", get_tags())
+
+            with new_context(fresh=False):
+                # Inner context should inherit outer tag
+                assert get_tags() == {"outer": "value"}
+
+            # After exiting context, inner tag should be gone
+            self.assertNotIn("inner", get_tags())
+
+            # Outer tag should still be there
+            assert get_tags()["outer"] == "value"
+
+    def test_nested_contexts(self):
+        with new_context(fresh=True):
+            tag("level1", "value1")
+
+            with new_context(fresh=True):
+                tag("level2", "value2")
+
+                with new_context(fresh=True):
+                    tag("level3", "value3")
+                    assert get_tags() == {"level3": "value3"}
+
+                # Back to level 2
+                assert get_tags() == {"level2": "value2"}
+
+            # Back to level 1
+            assert get_tags() == {"level1": "value1"}
+
+    @patch("posthog.capture_exception")
+    def test_scoped_decorator_success(self, mock_capture):
+        @scoped()
+        def successful_function(x, y):
+            tag("x", x)
+            tag("y", y)
+            return x + y
+
+        result = successful_function(1, 2)
+
+        # Function should execute normally
+        assert result == 3
+
+        # No exception should be captured
+        mock_capture.assert_not_called()
+
+        # Context should be cleared after function execution
+        assert get_tags() == {}
+
+    @patch("posthog.capture_exception")
+    def test_scoped_decorator_exception(self, mock_capture):
+        test_exception = ValueError("Test exception")
+
+        def check_context_on_capture(exception, **kwargs):
+            # Assert tags are available when capture_exception is called
+            current_tags = get_tags()
+            assert current_tags.get("important_context") == "value"
+
+        mock_capture.side_effect = check_context_on_capture
+
+        @scoped()
+        def failing_function():
+            tag("important_context", "value")
+            raise test_exception
+
+        # Function should raise the exception
+        with self.assertRaises(ValueError):
+            failing_function()
+
+        # Verify capture_exception was called
+        mock_capture.assert_called_once_with(test_exception)
+
+        # Context should be cleared after function execution
+        assert get_tags() == {}
+
+    @patch("posthog.capture_exception")
+    def test_new_context_exception_handling(self, mock_capture):
+        test_exception = RuntimeError("Context exception")
+
+        def check_context_on_capture(exception, **kwargs):
+            # Assert inner context tags are available when capture_exception is called
+            current_tags = get_tags()
+            assert current_tags.get("inner_context") == "inner_value"
+
+        mock_capture.side_effect = check_context_on_capture
+
+        # Set up outer context
+        with new_context():
+            tag("outer_context", "outer_value")
+
+            try:
+                with new_context():
+                    tag("inner_context", "inner_value")
+                    raise test_exception
+            except RuntimeError:
+                pass  # Expected exception
+
+            # Outer context should still be intact
+            assert get_tags()["outer_context"] == "outer_value"
+
+        # Verify capture_exception was called
+        mock_capture.assert_called_once_with(test_exception)
+
+    def test_identify_context(self):
+        with new_context(fresh=True):
+            # Initially no distinct ID
+            assert get_context_distinct_id() is None
+
+            # Set distinct ID
+            identify_context("user123")
+            assert get_context_distinct_id() == "user123"
+
+    def test_set_context_session(self):
+        with new_context(fresh=True):
+            # Initially no session ID
+            assert get_context_session_id() is None
+
+            # Set session ID
+            set_context_session("session456")
+            assert get_context_session_id() == "session456"
+
+    def test_context_inheritance_fresh_context(self):
+        with new_context(fresh=True):
+            identify_context("user123")
+            set_context_session("session456")
+
+            with new_context(fresh=True):
+                # Fresh context should not inherit
+                assert get_context_distinct_id() is None
+                assert get_context_session_id() is None
+
+            # Original context should still have values
+            assert get_context_distinct_id() == "user123"
+            assert get_context_session_id() == "session456"
+
+    def test_context_inheritance_non_fresh_context(self):
+        with new_context(fresh=True):
+            identify_context("user123")
+            set_context_session("session456")
+
+            with new_context(fresh=False):
+                # Non-fresh context should inherit
+                assert get_context_distinct_id() == "user123"
+                assert get_context_session_id() == "session456"
+
+                # Override in child context
+                identify_context("user789")
+                set_context_session("session999")
+                assert get_context_distinct_id() == "user789"
+                assert get_context_session_id() == "session999"
+
+            # Original context should still have original values
+            assert get_context_distinct_id() == "user123"
+            assert get_context_session_id() == "session456"
+
+    def test_child_tags_override_parent_tags_in_non_fresh_context(self):
+        with new_context(fresh=True):
+            tag("shared_key", "parent_value")
+            tag("parent_only", "parent")
+
+            with new_context(fresh=False):
+                # Child should inherit parent tags
+                assert get_tags()["parent_only"] == "parent"
+
+                # Child sets same key - should override parent
+                tag("shared_key", "child_value")
+                tag("child_only", "child")
+
+                tags = get_tags()
+                # Child value should win for shared key
+                assert tags["shared_key"] == "child_value"
+                # Both parent and child tags should be present
+                assert tags["parent_only"] == "parent"
+                assert tags["child_only"] == "child"
+
+            # Parent context should be unchanged
+            parent_tags = get_tags()
+            assert parent_tags["shared_key"] == "parent_value"
+            assert parent_tags["parent_only"] == "parent"
+            assert "child_only" not in parent_tags
+
+    def test_scoped_decorator_with_context_ids(self):
+        @scoped()
+        def function_with_context():
+            identify_context("user456")
+            set_context_session("session789")
+            return get_context_distinct_id(), get_context_session_id()
+
+        distinct_id, session_id = function_with_context()
+        assert distinct_id == "user456"
+        assert session_id == "session789"
+
+        # Context should be cleared after function execution
+        assert get_context_distinct_id() is None
+        assert get_context_session_id() is None

posthog/test/test_exception_capture.py

@@ -34,17 +34,72 @@ def test_excepthook(tmpdir):
     )
 
 
-def test_trying_to_use_django_integration(tmpdir):
+def test_code_variables_capture(tmpdir):
     app = tmpdir.join("app.py")
     app.write(
         dedent(
             """
-    from posthog import Posthog, Integrations
-    posthog = Posthog('phc_x', host='https://eu.i.posthog.com', enable_exception_autocapture=True, exception_autocapture_integrations=[Integrations.Django], debug=True, on_error=lambda e, batch: print('error handling batch: ', e, batch))
-
-    # frame_value = "LOL"
-
-    1/0
+    import os
+    from posthog import Posthog
+    
+    class UnserializableObject:
+        pass
+    
+    posthog = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=True,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def trigger_error():
+        my_string = "hello world"
+        my_number = 42
+        my_bool = True
+        my_dict = {"name": "test", "value": 123}
+        my_sensitive_dict = {
+            "safe_key": "safe_value",
+            "password": "secret123",  # key matches pattern -> should be masked
+            "other_key": "contains_password_here",  # value matches pattern -> should be masked
+        }
+        my_nested_dict = {
+            "level1": {
+                "level2": {
+                    "api_key": "nested_secret",  # deeply nested key matches
+                    "data": "contains_token_here",  # deeply nested value matches
+                    "safe": "visible",
+                }
+            }
+        }
+        my_list = ["safe_item", "has_password_inside", "another_safe"]
+        my_tuple = ("tuple_safe", "secret_in_value", "tuple_also_safe")
+        my_list_of_dicts = [
+            {"id": 1, "password": "list_dict_secret"},
+            {"id": 2, "value": "safe_value"},
+        ]
+        my_obj = UnserializableObject()
+        my_password = "secret123"  # Should be masked by default (name matches)
+        my_innocent_var = "contains_password_here"  # Should be masked by default (value matches)
+        __should_be_ignored = "hidden"  # Should be ignored by default
+        
+        1/0  # Trigger exception
+    
+    def intermediate_function():
+        request_id = "abc-123"
+        user_count = 100
+        is_active = True
+        
+        trigger_error()
+    
+    def process_data():
+        batch_size = 50
+        retry_count = 3
+        
+        intermediate_function()
+    
+    process_data()
     """
         )
     )
@@ -55,9 +110,343 @@ def test_trying_to_use_django_integration(tmpdir):
     output = excinfo.value.output
 
     assert b"ZeroDivisionError" in output
-    assert b"LOL" in output
-    assert b"DEBUG:posthog:data uploaded successfully" in output
+    assert b"code_variables" in output
+
+    # Variables from trigger_error frame
+    assert b"'my_string': 'hello world'" in output
+    assert b"'my_number': 42" in output
+    assert b"'my_bool': 'True'" in output
+    assert b'"my_dict": "{\\"name\\": \\"test\\", \\"value\\": 123}"' in output
     assert (
-        b'"$exception_list": [{"mechanism": {"type": "generic", "handled": true}, "module": null, "type": "ZeroDivisionError", "value": "division by zero", "stacktrace": {"frames": [{"platform": "python", "filename": "app.py", "abs_path"'
+        b'{\\"safe_key\\": \\"safe_value\\", \\"password\\": \\"$$_posthog_redacted_based_on_masking_rules_$$\\", \\"other_key\\": \\"$$_posthog_redacted_based_on_masking_rules_$$\\"}'
         in output
     )
+    assert (
+        b'{\\"level1\\": {\\"level2\\": {\\"api_key\\": \\"$$_posthog_redacted_based_on_masking_rules_$$\\", \\"data\\": \\"$$_posthog_redacted_based_on_masking_rules_$$\\", \\"safe\\": \\"visible\\"}}}'
+        in output
+    )
+    assert (
+        b'[\\"safe_item\\", \\"$$_posthog_redacted_based_on_masking_rules_$$\\", \\"another_safe\\"]'
+        in output
+    )
+    assert (
+        b'[\\"tuple_safe\\", \\"$$_posthog_redacted_based_on_masking_rules_$$\\", \\"tuple_also_safe\\"]'
+        in output
+    )
+    assert (
+        b'[{\\"id\\": 1, \\"password\\": \\"$$_posthog_redacted_based_on_masking_rules_$$\\"}, {\\"id\\": 2, \\"value\\": \\"safe_value\\"}]'
+        in output
+    )
+    assert b"<__main__.UnserializableObject object at" in output
+    assert b"'my_password': '$$_posthog_redacted_based_on_masking_rules_$$'" in output
+    assert (
+        b"'my_innocent_var': '$$_posthog_redacted_based_on_masking_rules_$$'" in output
+    )
+    assert b"'__should_be_ignored':" not in output
+
+    # Variables from intermediate_function frame
+    assert b"'request_id': 'abc-123'" in output
+    assert b"'user_count': 100" in output
+    assert b"'is_active': 'True'" in output
+
+    # Variables from process_data frame
+    assert b"'batch_size': 50" in output
+    assert b"'retry_count': 3" in output
+
+
+def test_code_variables_context_override(tmpdir):
+    app = tmpdir.join("app.py")
+    app.write(
+        dedent(
+            """
+    import os
+    import posthog
+    from posthog import Posthog
+    
+    posthog_client = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=False,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def process_data():
+        bank = "should_be_masked"
+        __dunder_var = "should_be_visible"
+        
+        1/0
+    
+    with posthog.new_context(client=posthog_client):
+        posthog.set_capture_exception_code_variables_context(True)
+        posthog.set_code_variables_mask_patterns_context([r"(?i).*bank.*"])
+        posthog.set_code_variables_ignore_patterns_context([])
+        
+        process_data()
+    """
+        )
+    )
+
+    with pytest.raises(subprocess.CalledProcessError) as excinfo:
+        subprocess.check_output([sys.executable, str(app)], stderr=subprocess.STDOUT)
+
+    output = excinfo.value.output
+
+    assert b"ZeroDivisionError" in output
+    assert b"code_variables" in output
+    assert b"'bank': '$$_posthog_redacted_based_on_masking_rules_$$'" in output
+    assert b"'__dunder_var': 'should_be_visible'" in output
+
+
+def test_code_variables_size_limiter(tmpdir):
+    app = tmpdir.join("app.py")
+    app.write(
+        dedent(
+            """
+    import os
+    from posthog import Posthog
+    
+    posthog = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=True,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def trigger_error():
+        var_a = "a" * 2000
+        var_b = "b" * 2000
+        var_c = "c" * 2000
+        var_d = "d" * 2000
+        var_e = "e" * 2000
+        var_f = "f" * 2000
+        var_g = "g" * 2000
+        
+        1/0
+    
+    def intermediate_function():
+        var_h = "h" * 2000
+        var_i = "i" * 2000
+        var_j = "j" * 2000
+        var_k = "k" * 2000
+        var_l = "l" * 2000
+        var_m = "m" * 2000
+        var_n = "n" * 2000
+        
+        trigger_error()
+    
+    def process_data():
+        var_o = "o" * 2000
+        var_p = "p" * 2000
+        var_q = "q" * 2000
+        var_r = "r" * 2000
+        var_s = "s" * 2000
+        var_t = "t" * 2000
+        var_u = "u" * 2000
+        
+        intermediate_function()
+    
+    process_data()
+    """
+        )
+    )
+
+    with pytest.raises(subprocess.CalledProcessError) as excinfo:
+        subprocess.check_output([sys.executable, str(app)], stderr=subprocess.STDOUT)
+
+    output = excinfo.value.output.decode("utf-8")
+
+    assert "ZeroDivisionError" in output
+    assert "code_variables" in output
+
+    captured_vars = []
+    for var_name in [
+        "var_a",
+        "var_b",
+        "var_c",
+        "var_d",
+        "var_e",
+        "var_f",
+        "var_g",
+        "var_h",
+        "var_i",
+        "var_j",
+        "var_k",
+        "var_l",
+        "var_m",
+        "var_n",
+        "var_o",
+        "var_p",
+        "var_q",
+        "var_r",
+        "var_s",
+        "var_t",
+        "var_u",
+    ]:
+        if f"'{var_name}'" in output:
+            captured_vars.append(var_name)
+
+    assert len(captured_vars) > 0
+    assert len(captured_vars) < 21
+
+
+def test_code_variables_disabled_capture(tmpdir):
+    app = tmpdir.join("app.py")
+    app.write(
+        dedent(
+            """
+    import os
+    from posthog import Posthog
+    
+    posthog = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=False,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def trigger_error():
+        my_string = "hello world"
+        my_number = 42
+        my_bool = True
+        
+        1/0
+    
+    trigger_error()
+    """
+        )
+    )
+
+    with pytest.raises(subprocess.CalledProcessError) as excinfo:
+        subprocess.check_output([sys.executable, str(app)], stderr=subprocess.STDOUT)
+
+    output = excinfo.value.output.decode("utf-8")
+
+    assert "ZeroDivisionError" in output
+    assert "'code_variables':" not in output
+    assert '"code_variables":' not in output
+    assert "'my_string'" not in output
+    assert "'my_number'" not in output
+
+
+def test_code_variables_enabled_then_disabled_in_context(tmpdir):
+    app = tmpdir.join("app.py")
+    app.write(
+        dedent(
+            """
+    import os
+    import posthog
+    from posthog import Posthog
+    
+    posthog_client = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=True,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def process_data():
+        my_var = "should not be captured"
+        important_value = 123
+        
+        1/0
+    
+    with posthog.new_context(client=posthog_client):
+        posthog.set_capture_exception_code_variables_context(False)
+        
+        process_data()
+    """
+        )
+    )
+
+    with pytest.raises(subprocess.CalledProcessError) as excinfo:
+        subprocess.check_output([sys.executable, str(app)], stderr=subprocess.STDOUT)
+
+    output = excinfo.value.output.decode("utf-8")
+
+    assert "ZeroDivisionError" in output
+    assert "'code_variables':" not in output
+    assert '"code_variables":' not in output
+    assert "'my_var'" not in output
+    assert "'important_value'" not in output
+
+
+def test_code_variables_repr_fallback(tmpdir):
+    app = tmpdir.join("app.py")
+    app.write(
+        dedent(
+            """
+    import os
+    import re
+    from datetime import datetime, timedelta
+    from decimal import Decimal
+    from fractions import Fraction
+    from posthog import Posthog
+    
+    class CustomReprClass:
+        def __repr__(self):
+            return '<CustomReprClass: custom representation>'
+    
+    posthog = Posthog(
+        'phc_x', 
+        host='https://eu.i.posthog.com', 
+        debug=True, 
+        enable_exception_autocapture=True,
+        capture_exception_code_variables=True,
+        project_root=os.path.dirname(os.path.abspath(__file__))
+    )
+    
+    def trigger_error():
+        my_regex = re.compile(r'\\d+')
+        my_datetime = datetime(2024, 1, 15, 10, 30, 45)
+        my_timedelta = timedelta(days=5, hours=3)
+        my_decimal = Decimal('123.456')
+        my_fraction = Fraction(3, 4)
+        my_set = {1, 2, 3}
+        my_frozenset = frozenset([4, 5, 6])
+        my_bytes = b'hello bytes'
+        my_bytearray = bytearray(b'mutable bytes')
+        my_memoryview = memoryview(b'memory view')
+        my_complex = complex(3, 4)
+        my_range = range(10)
+        my_custom = CustomReprClass()
+        my_lambda = lambda x: x * 2
+        my_function = trigger_error
+        
+        1/0
+    
+    trigger_error()
+    """
+        )
+    )
+
+    with pytest.raises(subprocess.CalledProcessError) as excinfo:
+        subprocess.check_output([sys.executable, str(app)], stderr=subprocess.STDOUT)
+
+    output = excinfo.value.output.decode("utf-8")
+
+    assert "ZeroDivisionError" in output
+    assert "code_variables" in output
+
+    assert "re.compile(" in output and "\\\\d+" in output
+    assert "datetime.datetime(2024, 1, 15, 10, 30, 45)" in output
+    assert "datetime.timedelta(days=5, seconds=10800)" in output
+    assert "Decimal('123.456')" in output
+    assert "Fraction(3, 4)" in output
+    assert "{1, 2, 3}" in output
+    assert "frozenset({4, 5, 6})" in output
+    assert "b'hello bytes'" in output
+    assert "bytearray(b'mutable bytes')" in output
+    assert "<memory at" in output
+    assert "(3+4j)" in output
+    assert "range(0, 10)" in output
+    assert "<CustomReprClass: custom representation>" in output
+    assert "<lambda>" in output
+    assert "<function trigger_error at" in output

posthog/test/test_feature_flag.py

@@ -10,8 +10,17 @@ class TestFeatureFlag(unittest.TestCase):
             "key": "test-flag",
             "enabled": True,
             "variant": "test-variant",
-            "reason": {"code": "matched_condition", "condition_index": 0, "description": "Matched condition set 1"},
-            "metadata": {"id": 1, "payload": '{"some": "json"}', "version": 2, "description": "test-description"},
+            "reason": {
+                "code": "matched_condition",
+                "condition_index": 0,
+                "description": "Matched condition set 1",
+            },
+            "metadata": {
+                "id": 1,
+                "payload": '{"some": "json"}',
+                "version": 2,
+                "description": "test-description",
+            },
         }
 
         flag = FeatureFlag.from_json(resp)
@@ -20,10 +29,21 @@ class TestFeatureFlag(unittest.TestCase):
         self.assertEqual(flag.variant, "test-variant")
         self.assertEqual(flag.get_value(), "test-variant")
         self.assertEqual(
-            flag.reason, FlagReason(code="matched_condition", condition_index=0, description="Matched condition set 1")
+            flag.reason,
+            FlagReason(
+                code="matched_condition",
+                condition_index=0,
+                description="Matched condition set 1",
+            ),
         )
         self.assertEqual(
-            flag.metadata, FlagMetadata(id=1, payload='{"some": "json"}', version=2, description="test-description")
+            flag.metadata,
+            FlagMetadata(
+                id=1,
+                payload='{"some": "json"}',
+                version=2,
+                description="test-description",
+            ),
         )
 
     def test_feature_flag_from_json_minimal(self):
@@ -44,7 +64,11 @@ class TestFeatureFlag(unittest.TestCase):
             "key": "test-flag",
             "enabled": True,
             "variant": "test-variant",
-            "reason": {"code": "matched_condition", "condition_index": 0, "description": "Matched condition set 1"},
+            "reason": {
+                "code": "matched_condition",
+                "condition_index": 0,
+                "description": "Matched condition set 1",
+            },
         }
 
         flag = FeatureFlag.from_json(resp)
@@ -53,13 +77,22 @@ class TestFeatureFlag(unittest.TestCase):
         self.assertEqual(flag.variant, "test-variant")
         self.assertEqual(flag.get_value(), "test-variant")
         self.assertEqual(
-            flag.reason, FlagReason(code="matched_condition", condition_index=0, description="Matched condition set 1")
+            flag.reason,
+            FlagReason(
+                code="matched_condition",
+                condition_index=0,
+                description="Matched condition set 1",
+            ),
         )
         self.assertEqual(flag.metadata, LegacyFlagMetadata(payload=None))
 
     def test_flag_reason_from_json(self):
         # Test with complete data
-        resp = {"code": "user_in_segment", "condition_index": 1, "description": "User is in segment 'beta_users'"}
+        resp = {
+            "code": "user_in_segment",
+            "condition_index": 1,
+            "description": "User is in segment 'beta_users'",
+        }
         reason = FlagReason.from_json(resp)
         self.assertEqual(reason.code, "user_in_segment")
         self.assertEqual(reason.condition_index, 1)
@@ -77,7 +110,12 @@ class TestFeatureFlag(unittest.TestCase):
 
     def test_flag_metadata_from_json(self):
         # Test with complete data
-        resp = {"id": 123, "payload": {"key": "value"}, "version": 1, "description": "Test flag"}
+        resp = {
+            "id": 123,
+            "payload": {"key": "value"},
+            "version": 1,
+            "description": "Test flag",
+        }
         metadata = FlagMetadata.from_json(resp)
         self.assertEqual(metadata.id, 123)
         self.assertEqual(metadata.payload, {"key": "value"})
@@ -106,7 +144,12 @@ class TestFeatureFlag(unittest.TestCase):
                 "condition_index": 1,
                 "description": "User is in segment 'beta_users'",
             },
-            "metadata": {"id": 123, "payload": {"key": "value"}, "version": 1, "description": "Test flag"},
+            "metadata": {
+                "id": 123,
+                "payload": {"key": "value"},
+                "version": 1,
+                "description": "Test flag",
+            },
         }
         flag = FeatureFlag.from_json(resp)
         self.assertEqual(flag.key, "test-flag")
@@ -131,7 +174,11 @@ class TestFeatureFlag(unittest.TestCase):
 
     def test_feature_flag_from_json_with_reason(self):
         # Test with reason but no metadata
-        resp = {"key": "test-flag", "enabled": True, "reason": {"code": "user_in_segment"}}
+        resp = {
+            "key": "test-flag",
+            "enabled": True,
+            "reason": {"code": "user_in_segment"},
+        }
         flag = FeatureFlag.from_json(resp)
         self.assertEqual(flag.key, "test-flag")
         self.assertTrue(flag.enabled)

posthog/test/test_feature_flag_result.py

@@ -4,12 +4,20 @@ import mock
 
 from posthog.client import Client
 from posthog.test.test_utils import FAKE_TEST_API_KEY
-from posthog.types import FeatureFlag, FeatureFlagResult, FlagMetadata, FlagReason
+from posthog.types import (
+    FeatureFlag,
+    FeatureFlagError,
+    FeatureFlagResult,
+    FlagMetadata,
+    FlagReason,
+)
 
 
 class TestFeatureFlagResult(unittest.TestCase):
     def test_from_bool_value_and_payload(self):
-        result = FeatureFlagResult.from_value_and_payload("test-flag", True, "[1, 2, 3]")
+        result = FeatureFlagResult.from_value_and_payload(
+            "test-flag", True, "[1, 2, 3]"
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, True)
@@ -17,7 +25,9 @@ class TestFeatureFlagResult(unittest.TestCase):
         self.assertEqual(result.payload, [1, 2, 3])
 
     def test_from_false_value_and_payload(self):
-        result = FeatureFlagResult.from_value_and_payload("test-flag", False, '{"some": "value"}')
+        result = FeatureFlagResult.from_value_and_payload(
+            "test-flag", False, '{"some": "value"}'
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, False)
@@ -25,7 +35,9 @@ class TestFeatureFlagResult(unittest.TestCase):
         self.assertEqual(result.payload, {"some": "value"})
 
     def test_from_variant_value_and_payload(self):
-        result = FeatureFlagResult.from_value_and_payload("test-flag", "control", "true")
+        result = FeatureFlagResult.from_value_and_payload(
+            "test-flag", "control", "true"
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, True)
@@ -33,7 +45,9 @@ class TestFeatureFlagResult(unittest.TestCase):
         self.assertEqual(result.payload, True)
 
     def test_from_none_value_and_payload(self):
-        result = FeatureFlagResult.from_value_and_payload("test-flag", None, '{"some": "value"}')
+        result = FeatureFlagResult.from_value_and_payload(
+            "test-flag", None, '{"some": "value"}'
+        )
         self.assertIsNone(result)
 
     def test_from_boolean_flag_details(self):
@@ -41,8 +55,12 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant=None,
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload='"Some string"'),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload='"Some string"'
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
         result = FeatureFlagResult.from_flag_details(flag_details)
@@ -57,11 +75,17 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant=None,
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload='"Some string"'),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload='"Some string"'
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
-        result = FeatureFlagResult.from_flag_details(flag_details, override_match_value="control")
+        result = FeatureFlagResult.from_flag_details(
+            flag_details, override_match_value="control"
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, True)
@@ -73,11 +97,17 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant="control",
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload='{"some": "value"}'),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload='{"some": "value"}'
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
-        result = FeatureFlagResult.from_flag_details(flag_details, override_match_value=True)
+        result = FeatureFlagResult.from_flag_details(
+            flag_details, override_match_value=True
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, True)
@@ -89,11 +119,17 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant="control",
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload='{"some": "value"}'),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload='{"some": "value"}'
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
-        result = FeatureFlagResult.from_flag_details(flag_details, override_match_value=False)
+        result = FeatureFlagResult.from_flag_details(
+            flag_details, override_match_value=False
+        )
 
         self.assertEqual(result.key, "test-flag")
         self.assertEqual(result.enabled, False)
@@ -105,8 +141,12 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant="control",
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload='{"some": "value"}'),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload='{"some": "value"}'
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
         result = FeatureFlagResult.from_flag_details(flag_details)
@@ -126,8 +166,12 @@ class TestFeatureFlagResult(unittest.TestCase):
             key="test-flag",
             enabled=True,
             variant=None,
-            metadata=FlagMetadata(id=1, version=1, description="test-flag", payload=None),
-            reason=FlagReason(code="test-reason", description="test-reason", condition_index=0),
+            metadata=FlagMetadata(
+                id=1, version=1, description="test-flag", payload=None
+            ),
+            reason=FlagReason(
+                code="test-reason", description="test-reason", condition_index=0
+            ),
         )
 
         result = FeatureFlagResult.from_flag_details(flag_details)
@@ -151,7 +195,6 @@ class TestGetFeatureFlagResult(unittest.TestCase):
 
     def set_fail(self, e, batch):
         """Mark the failure handler"""
-        print("FAIL", e, batch)  # noqa: T201
         self.failed = True
 
     def setUp(self):
@@ -191,9 +234,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
         self.assertEqual(flag_result.variant, None)
         self.assertEqual(flag_result.payload, 300)
         patch_capture.assert_called_with(
-            "some-distinct-id",
             "$feature_flag_called",
-            {
+            distinct_id="some-distinct-id",
+            properties={
                 "$feature_flag": "person-flag",
                 "$feature_flag_response": True,
                 "locally_evaluated": True,
@@ -203,6 +246,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             groups={},
             disable_geoip=None,
         )
+        # Verify error property is NOT present on successful evaluation
+        captured_properties = patch_capture.call_args[1]["properties"]
+        self.assertNotIn("$feature_flag_error", captured_properties)
 
     @mock.patch.object(Client, "capture")
     def test_get_feature_flag_result_variant_local_evaluation(self, patch_capture):
@@ -245,9 +291,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
         self.assertEqual(flag_result.payload, {"some": "value"})
 
         patch_capture.assert_called_with(
-            "distinct_id",
             "$feature_flag_called",
-            {
+            distinct_id="distinct_id",
+            properties={
                 "$feature_flag": "person-flag",
                 "$feature_flag_response": "variant-1",
                 "locally_evaluated": True,
@@ -257,6 +303,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             groups={},
             disable_geoip=None,
         )
+        # Verify error property is NOT present on successful evaluation
+        captured_properties = patch_capture.call_args[1]["properties"]
+        self.assertNotIn("$feature_flag_error", captured_properties)
 
         another_flag_result = self.client.get_feature_flag_result(
             "person-flag", "another-distinct-id", person_properties={"region": "USA"}
@@ -267,9 +316,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
         self.assertIsNone(another_flag_result.payload)
 
         patch_capture.assert_called_with(
-            "another-distinct-id",
             "$feature_flag_called",
-            {
+            distinct_id="another-distinct-id",
+            properties={
                 "$feature_flag": "person-flag",
                 "$feature_flag_response": "variant-2",
                 "locally_evaluated": True,
@@ -300,14 +349,16 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             },
         }
 
-        flag_result = self.client.get_feature_flag_result("person-flag", "some-distinct-id")
+        flag_result = self.client.get_feature_flag_result(
+            "person-flag", "some-distinct-id"
+        )
         self.assertEqual(flag_result.enabled, True)
         self.assertEqual(flag_result.variant, None)
         self.assertEqual(flag_result.payload, 300)
         patch_capture.assert_called_with(
-            "some-distinct-id",
             "$feature_flag_called",
-            {
+            distinct_id="some-distinct-id",
+            properties={
                 "$feature_flag": "person-flag",
                 "$feature_flag_response": True,
                 "locally_evaluated": False,
@@ -320,6 +371,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             groups={},
             disable_geoip=None,
         )
+        # Verify error property is NOT present on successful evaluation
+        captured_properties = patch_capture.call_args[1]["properties"]
+        self.assertNotIn("$feature_flag_error", captured_properties)
 
     @mock.patch("posthog.client.flags")
     @mock.patch.object(Client, "capture")
@@ -348,9 +402,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
         self.assertEqual(flag_result.get_value(), "variant-1")
         self.assertEqual(flag_result.payload, [1, 2, 3])
         patch_capture.assert_called_with(
-            "distinct_id",
             "$feature_flag_called",
-            {
+            distinct_id="distinct_id",
+            properties={
                 "$feature_flag": "person-flag",
                 "$feature_flag_response": "variant-1",
                 "locally_evaluated": False,
@@ -363,6 +417,9 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             groups={},
             disable_geoip=None,
         )
+        # Verify error property is NOT present on successful evaluation
+        captured_properties = patch_capture.call_args[1]["properties"]
+        self.assertNotIn("$feature_flag_error", captured_properties)
 
     @mock.patch("posthog.client.flags")
     @mock.patch.object(Client, "capture")
@@ -385,17 +442,441 @@ class TestGetFeatureFlagResult(unittest.TestCase):
             },
         }
 
-        flag_result = self.client.get_feature_flag_result("no-person-flag", "some-distinct-id")
+        flag_result = self.client.get_feature_flag_result(
+            "no-person-flag", "some-distinct-id"
+        )
 
         self.assertIsNone(flag_result)
         patch_capture.assert_called_with(
-            "some-distinct-id",
             "$feature_flag_called",
-            {
+            distinct_id="some-distinct-id",
+            properties={
                 "$feature_flag": "no-person-flag",
                 "$feature_flag_response": None,
                 "locally_evaluated": False,
                 "$feature/no-person-flag": None,
+                "$feature_flag_error": FeatureFlagError.FLAG_MISSING,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_with_errors_while_computing_flags(
+        self, patch_capture, patch_flags
+    ):
+        """Test that errors_while_computing_flags is included in the $feature_flag_called event.
+
+        When the server returns errorsWhileComputingFlags=true, it indicates that there
+        was an error computing one or more flags. We include this in the event so users
+        can identify and debug flag evaluation issues.
+        """
+        patch_flags.return_value = {
+            "flags": {
+                "my-flag": {
+                    "key": "my-flag",
+                    "enabled": True,
+                    "variant": None,
+                    "reason": {"description": "Matched condition set 1"},
+                    "metadata": {"id": 1, "version": 1, "payload": None},
+                },
+            },
+            "requestId": "test-request-id-789",
+            "errorsWhileComputingFlags": True,
+        }
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertEqual(flag_result.enabled, True)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": True,
+                "locally_evaluated": False,
+                "$feature/my-flag": True,
+                "$feature_flag_request_id": "test-request-id-789",
+                "$feature_flag_reason": "Matched condition set 1",
+                "$feature_flag_id": 1,
+                "$feature_flag_version": 1,
+                "$feature_flag_error": FeatureFlagError.ERRORS_WHILE_COMPUTING,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_flag_not_in_response(
+        self, patch_capture, patch_flags
+    ):
+        """Test that when a flag is not in the API response, we capture flag_missing error.
+
+        This happens when a flag doesn't exist or the user doesn't match any conditions.
+        """
+        patch_flags.return_value = {
+            "flags": {
+                "other-flag": {
+                    "key": "other-flag",
+                    "enabled": True,
+                    "variant": None,
+                    "reason": {"description": "Matched condition set 1"},
+                    "metadata": {"id": 1, "version": 1, "payload": None},
+                },
+            },
+            "requestId": "test-request-id-456",
+        }
+
+        flag_result = self.client.get_feature_flag_result(
+            "missing-flag", "some-distinct-id"
+        )
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "missing-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/missing-flag": None,
+                "$feature_flag_request_id": "test-request-id-456",
+                "$feature_flag_error": FeatureFlagError.FLAG_MISSING,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_errors_computing_and_flag_missing(
+        self, patch_capture, patch_flags
+    ):
+        """Test that both errors are reported when errorsWhileComputingFlags=true AND flag is missing.
+
+        This can happen when the server encounters errors computing flags AND the requested
+        flag is not in the response. Both conditions should be reported for debugging.
+        """
+        patch_flags.return_value = {
+            "flags": {},  # Flag is missing
+            "requestId": "test-request-id-999",
+            "errorsWhileComputingFlags": True,  # But errors also occurred
+        }
+
+        flag_result = self.client.get_feature_flag_result(
+            "missing-flag", "some-distinct-id"
+        )
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "missing-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/missing-flag": None,
+                "$feature_flag_request_id": "test-request-id-999",
+                "$feature_flag_error": f"{FeatureFlagError.ERRORS_WHILE_COMPUTING},{FeatureFlagError.FLAG_MISSING}",
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_unknown_error(self, patch_capture, patch_flags):
+        """Test that unexpected exceptions are captured as unknown_error."""
+        patch_flags.side_effect = Exception("Unexpected error")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.UNKNOWN_ERROR,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_timeout_error(self, patch_capture, patch_flags):
+        """Test that timeout errors are captured specifically."""
+        from posthog.request import RequestsTimeout
+
+        patch_flags.side_effect = RequestsTimeout("Request timed out")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.TIMEOUT,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_connection_error(self, patch_capture, patch_flags):
+        """Test that connection errors are captured specifically."""
+        from posthog.request import RequestsConnectionError
+
+        patch_flags.side_effect = RequestsConnectionError("Connection refused")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.CONNECTION_ERROR,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_api_error(self, patch_capture, patch_flags):
+        """Test that API errors include the status code."""
+        from posthog.request import APIError
+
+        patch_flags.side_effect = APIError(500, "Internal server error")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.api_error(500),
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_get_feature_flag_result_quota_limited(self, patch_capture, patch_flags):
+        """Test that quota limit errors are captured specifically."""
+        from posthog.request import QuotaLimitError
+
+        patch_flags.side_effect = QuotaLimitError(429, "Rate limit exceeded")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        self.assertIsNone(flag_result)
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.QUOTA_LIMITED,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+
+class TestFeatureFlagErrorWithStaleCacheFallback(unittest.TestCase):
+    """Tests for stale cache fallback behavior when flag evaluation fails.
+
+    When the PostHog API is unavailable (timeout, connection error, etc.), the SDK
+    falls back to stale cached flag values if available. These tests verify that:
+    1. The stale cached value is returned when an error occurs
+    2. The $feature_flag_error property is still set (for debugging)
+    3. The response reflects the cached value, not None
+    """
+
+    def set_fail(self, e, batch):
+        """Mark the failure handler"""
+        self.failed = True
+
+    def setUp(self):
+        self.failed = False
+        # Create client with memory-based flag cache enabled
+        self.client = Client(
+            FAKE_TEST_API_KEY,
+            on_error=self.set_fail,
+            flag_fallback_cache_url="memory://local/?ttl=300&size=10000",
+        )
+
+    def _populate_stale_cache(self, distinct_id, flag_key, flag_result):
+        """Pre-populate the flag cache with a value that will be used for stale fallback."""
+        self.client.flag_cache.set_cached_flag(
+            distinct_id,
+            flag_key,
+            flag_result,
+            flag_definition_version=self.client.flag_definition_version,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_timeout_error_returns_stale_cached_value(self, patch_capture, patch_flags):
+        """Test that timeout errors return stale cached value when available."""
+        from posthog.request import RequestsTimeout
+
+        # Pre-populate cache with a flag result
+        cached_result = FeatureFlagResult.from_value_and_payload(
+            "my-flag", "cached-variant", '{"from": "cache"}'
+        )
+        self._populate_stale_cache("some-distinct-id", "my-flag", cached_result)
+
+        # Simulate timeout error
+        patch_flags.side_effect = RequestsTimeout("Request timed out")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        # Should return the stale cached value
+        self.assertIsNotNone(flag_result)
+        self.assertEqual(flag_result.variant, "cached-variant")
+        self.assertEqual(flag_result.payload, {"from": "cache"})
+
+        # Error should still be tracked for debugging
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": "cached-variant",
+                "locally_evaluated": False,
+                "$feature/my-flag": "cached-variant",
+                "$feature_flag_payload": {"from": "cache"},
+                "$feature_flag_error": FeatureFlagError.TIMEOUT,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_connection_error_returns_stale_cached_value(
+        self, patch_capture, patch_flags
+    ):
+        """Test that connection errors return stale cached value when available."""
+        from posthog.request import RequestsConnectionError
+
+        # Pre-populate cache with a boolean flag result
+        cached_result = FeatureFlagResult.from_value_and_payload("my-flag", True, None)
+        self._populate_stale_cache("some-distinct-id", "my-flag", cached_result)
+
+        # Simulate connection error
+        patch_flags.side_effect = RequestsConnectionError("Connection refused")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        # Should return the stale cached value
+        self.assertIsNotNone(flag_result)
+        self.assertEqual(flag_result.enabled, True)
+        self.assertIsNone(flag_result.variant)
+
+        # Error should still be tracked
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": True,
+                "locally_evaluated": False,
+                "$feature/my-flag": True,
+                "$feature_flag_error": FeatureFlagError.CONNECTION_ERROR,
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_api_error_returns_stale_cached_value(self, patch_capture, patch_flags):
+        """Test that API errors return stale cached value when available."""
+        from posthog.request import APIError
+
+        # Pre-populate cache
+        cached_result = FeatureFlagResult.from_value_and_payload(
+            "my-flag", "control", None
+        )
+        self._populate_stale_cache("some-distinct-id", "my-flag", cached_result)
+
+        # Simulate API error
+        patch_flags.side_effect = APIError(503, "Service unavailable")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        # Should return the stale cached value
+        self.assertIsNotNone(flag_result)
+        self.assertEqual(flag_result.variant, "control")
+
+        # Error should still be tracked with status code
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": "control",
+                "locally_evaluated": False,
+                "$feature/my-flag": "control",
+                "$feature_flag_error": FeatureFlagError.api_error(503),
+            },
+            groups={},
+            disable_geoip=None,
+        )
+
+    @mock.patch("posthog.client.flags")
+    @mock.patch.object(Client, "capture")
+    def test_error_without_cache_returns_none(self, patch_capture, patch_flags):
+        """Test that errors return None when no stale cache is available."""
+        from posthog.request import RequestsTimeout
+
+        # Do NOT populate cache - no fallback available
+
+        patch_flags.side_effect = RequestsTimeout("Request timed out")
+
+        flag_result = self.client.get_feature_flag_result("my-flag", "some-distinct-id")
+
+        # Should return None since no cache available
+        self.assertIsNone(flag_result)
+
+        # Error should still be tracked
+        patch_capture.assert_called_with(
+            "$feature_flag_called",
+            distinct_id="some-distinct-id",
+            properties={
+                "$feature_flag": "my-flag",
+                "$feature_flag_response": None,
+                "locally_evaluated": False,
+                "$feature/my-flag": None,
+                "$feature_flag_error": FeatureFlagError.TIMEOUT,
             },
             groups={},
             disable_geoip=None,

posthog/test/test_flag_definition_cache.py

@@ -0,0 +1,612 @@
+"""
+Tests for FlagDefinitionCacheProvider functionality.
+
+These tests follow the patterns from the TypeScript implementation in posthog-js/packages/node.
+"""
+
+import threading
+import unittest
+from typing import Optional
+from unittest import mock
+
+from posthog.client import Client
+from posthog.flag_definition_cache import (
+    FlagDefinitionCacheData,
+    FlagDefinitionCacheProvider,
+)
+from posthog.request import GetResponse
+from posthog.test.test_utils import FAKE_TEST_API_KEY
+
+
+class MockCacheProvider:
+    """A mock implementation of FlagDefinitionCacheProvider for testing."""
+
+    def __init__(self):
+        self.stored_data: Optional[FlagDefinitionCacheData] = None
+        self.should_fetch_return_value = True
+        self.get_call_count = 0
+        self.should_fetch_call_count = 0
+        self.on_received_call_count = 0
+        self.shutdown_call_count = 0
+        self.should_fetch_error: Optional[Exception] = None
+        self.get_error: Optional[Exception] = None
+        self.on_received_error: Optional[Exception] = None
+        self.shutdown_error: Optional[Exception] = None
+
+    def get_flag_definitions(self) -> Optional[FlagDefinitionCacheData]:
+        self.get_call_count += 1
+        if self.get_error:
+            raise self.get_error
+        return self.stored_data
+
+    def should_fetch_flag_definitions(self) -> bool:
+        self.should_fetch_call_count += 1
+        if self.should_fetch_error:
+            raise self.should_fetch_error
+        return self.should_fetch_return_value
+
+    def on_flag_definitions_received(self, data: FlagDefinitionCacheData) -> None:
+        self.on_received_call_count += 1
+        if self.on_received_error:
+            raise self.on_received_error
+        self.stored_data = data
+
+    def shutdown(self) -> None:
+        self.shutdown_call_count += 1
+        if self.shutdown_error:
+            raise self.shutdown_error
+
+
+class TestFlagDefinitionCacheProvider(unittest.TestCase):
+    """Tests for the FlagDefinitionCacheProvider protocol."""
+
+    @classmethod
+    def setUpClass(cls):
+        # Prevent real HTTP requests
+        cls.client_post_patcher = mock.patch("posthog.client.batch_post")
+        cls.consumer_post_patcher = mock.patch("posthog.consumer.batch_post")
+        cls.client_post_patcher.start()
+        cls.consumer_post_patcher.start()
+
+    @classmethod
+    def tearDownClass(cls):
+        cls.client_post_patcher.stop()
+        cls.consumer_post_patcher.stop()
+
+    def setUp(self):
+        self.cache_provider = MockCacheProvider()
+        self.sample_flags_data: FlagDefinitionCacheData = {
+            "flags": [
+                {"key": "test-flag", "active": True, "filters": {}},
+                {"key": "another-flag", "active": False, "filters": {}},
+            ],
+            "group_type_mapping": {"0": "company", "1": "project"},
+            "cohorts": {"1": {"properties": []}},
+        }
+
+    def tearDown(self):
+        # Ensure client cleanup
+        pass
+
+    def _create_client_with_cache(self) -> Client:
+        """Create a client with the mock cache provider."""
+        return Client(
+            FAKE_TEST_API_KEY,
+            personal_api_key="test-personal-key",
+            flag_definition_cache_provider=self.cache_provider,
+            sync_mode=True,
+            enable_local_evaluation=False,  # Disable poller for tests
+        )
+
+
+class TestCacheInitialization(TestFlagDefinitionCacheProvider):
+    """Tests for cache initialization behavior."""
+
+    @mock.patch("posthog.client.get")
+    def test_uses_cached_data_when_should_fetch_returns_false(self, mock_get):
+        """When should_fetch returns False and cache has data, use cached data."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = self.sample_flags_data
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should not call API
+        mock_get.assert_not_called()
+
+        # Should have called cache methods
+        self.assertEqual(self.cache_provider.should_fetch_call_count, 1)
+        self.assertEqual(self.cache_provider.get_call_count, 1)
+
+        # Flags should be loaded from cache
+        self.assertEqual(len(client.feature_flags), 2)
+        self.assertEqual(client.feature_flags[0]["key"], "test-flag")
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_fetches_from_api_when_should_fetch_returns_true(self, mock_get):
+        """When should_fetch returns True, fetch from API."""
+        self.cache_provider.should_fetch_return_value = True
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should call API
+        mock_get.assert_called_once()
+
+        # Should have called should_fetch but not get
+        self.assertEqual(self.cache_provider.should_fetch_call_count, 1)
+        self.assertEqual(self.cache_provider.get_call_count, 0)
+
+        # Should have called on_received to store in cache
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_emergency_fallback_when_cache_empty_and_no_flags(self, mock_get):
+        """When should_fetch=False but cache is empty and no flags loaded, fetch anyway."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = None  # Empty cache
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should call API due to emergency fallback
+        mock_get.assert_called_once()
+
+        # Should have called on_received
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_preserves_existing_flags_when_cache_returns_none(self, mock_get):
+        """When cache returns None but client has flags, preserve existing flags."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = None  # Empty cache
+
+        client = self._create_client_with_cache()
+
+        # Pre-load flags (simulating a previous successful fetch)
+        client.feature_flags = self.sample_flags_data["flags"]
+        client.group_type_mapping = self.sample_flags_data["group_type_mapping"]
+        client.cohorts = self.sample_flags_data["cohorts"]
+
+        client._load_feature_flags()
+
+        # Should NOT call API since we already have flags
+        mock_get.assert_not_called()
+
+        # Existing flags should be preserved
+        self.assertEqual(len(client.feature_flags), 2)
+        self.assertEqual(client.feature_flags[0]["key"], "test-flag")
+
+        client.join()
+
+
+class TestFetchCoordination(TestFlagDefinitionCacheProvider):
+    """Tests for fetch coordination between workers."""
+
+    @mock.patch("posthog.client.get")
+    def test_calls_should_fetch_before_each_poll(self, mock_get):
+        """should_fetch_flag_definitions is called before each poll cycle."""
+        self.cache_provider.should_fetch_return_value = True
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+
+        # First poll
+        client._load_feature_flags()
+        self.assertEqual(self.cache_provider.should_fetch_call_count, 1)
+
+        # Second poll
+        client._load_feature_flags()
+        self.assertEqual(self.cache_provider.should_fetch_call_count, 2)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_does_not_call_on_received_when_fetch_skipped(self, mock_get):
+        """on_flag_definitions_received is NOT called when fetch is skipped."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = self.sample_flags_data
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should not call on_received since we didn't fetch
+        self.assertEqual(self.cache_provider.on_received_call_count, 0)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_stores_data_in_cache_after_api_fetch(self, mock_get):
+        """on_flag_definitions_received receives the fetched data."""
+        self.cache_provider.should_fetch_return_value = True
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should have stored data in cache
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+        self.assertIsNotNone(self.cache_provider.stored_data)
+        self.assertEqual(len(self.cache_provider.stored_data["flags"]), 2)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_304_not_modified_does_not_update_cache(self, mock_get):
+        """When API returns 304 Not Modified, cache should not be updated."""
+        self.cache_provider.should_fetch_return_value = True
+
+        # First fetch to populate flags and ETag
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Verify initial fetch worked
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+        self.assertEqual(len(client.feature_flags), 2)
+
+        # Second fetch returns 304 Not Modified
+        mock_get.return_value = GetResponse(
+            data=None, etag="test-etag", not_modified=True
+        )
+
+        client._load_feature_flags()
+
+        # API was called twice
+        self.assertEqual(mock_get.call_count, 2)
+
+        # should_fetch was called twice
+        self.assertEqual(self.cache_provider.should_fetch_call_count, 2)
+
+        # on_received should NOT be called again (304 = no new data)
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+
+        # Flags should still be present
+        self.assertEqual(len(client.feature_flags), 2)
+
+        client.join()
+
+
+class TestErrorHandling(TestFlagDefinitionCacheProvider):
+    """Tests for error handling in cache provider operations."""
+
+    @mock.patch("posthog.client.get")
+    def test_should_fetch_error_defaults_to_fetching(self, mock_get):
+        """When should_fetch throws an error, default to fetching from API."""
+        self.cache_provider.should_fetch_error = Exception("Lock acquisition failed")
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should still fetch from API
+        mock_get.assert_called_once()
+
+        # Flags should be loaded
+        self.assertEqual(len(client.feature_flags), 2)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_get_error_falls_back_to_api_fetch(self, mock_get):
+        """When get_flag_definitions throws an error, fetch from API."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.get_error = Exception("Cache read failed")
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should fall back to API
+        mock_get.assert_called_once()
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_on_received_error_keeps_flags_in_memory(self, mock_get):
+        """When on_flag_definitions_received throws, flags are still in memory."""
+        self.cache_provider.should_fetch_return_value = True
+        self.cache_provider.on_received_error = Exception("Cache write failed")
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Flags should still be loaded in memory despite cache error
+        self.assertEqual(len(client.feature_flags), 2)
+        self.assertEqual(client.feature_flags[0]["key"], "test-flag")
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_shutdown_error_is_logged_but_continues(self, mock_get):
+        """When shutdown throws an error, it's logged but shutdown continues."""
+        self.cache_provider.shutdown_error = Exception("Lock release failed")
+
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Should not raise when joining
+        client.join()
+
+        # Shutdown was called
+        self.assertEqual(self.cache_provider.shutdown_call_count, 1)
+
+
+class TestShutdownLifecycle(TestFlagDefinitionCacheProvider):
+    """Tests for shutdown lifecycle."""
+
+    @mock.patch("posthog.client.get")
+    def test_shutdown_calls_cache_provider_shutdown(self, mock_get):
+        """Client shutdown calls cache provider shutdown."""
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Shutdown
+        client.join()
+
+        self.assertEqual(self.cache_provider.shutdown_call_count, 1)
+
+    @mock.patch("posthog.client.get")
+    def test_shutdown_called_even_without_fetching(self, mock_get):
+        """Shutdown is called even when cache was used instead of fetching."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = self.sample_flags_data
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+        client.join()
+
+        # Shutdown should still be called
+        self.assertEqual(self.cache_provider.shutdown_call_count, 1)
+
+    @mock.patch("posthog.client.get")
+    def test_multiple_join_calls_only_shutdown_once(self, mock_get):
+        """Calling join() multiple times should only call cache provider shutdown once."""
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Call join multiple times
+        client.join()
+        client.join()
+        client.join()
+
+        # Shutdown should be called each time (current behavior - no guard)
+        # This test documents the current behavior
+        self.assertGreaterEqual(self.cache_provider.shutdown_call_count, 1)
+
+
+class TestBackwardCompatibility(TestFlagDefinitionCacheProvider):
+    """Tests for backward compatibility without cache provider."""
+
+    @mock.patch("posthog.client.get")
+    def test_works_without_cache_provider(self, mock_get):
+        """Client works normally without a cache provider configured."""
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        # Create client without cache provider
+        client = Client(
+            FAKE_TEST_API_KEY,
+            personal_api_key="test-personal-key",
+            sync_mode=True,
+            enable_local_evaluation=False,
+        )
+        client._load_feature_flags()
+
+        # Should fetch from API
+        mock_get.assert_called_once()
+
+        # Flags should be loaded
+        self.assertEqual(len(client.feature_flags), 2)
+
+        client.join()
+
+
+class TestDataIntegrity(TestFlagDefinitionCacheProvider):
+    """Tests for data integrity between cache and client state."""
+
+    @mock.patch("posthog.client.get")
+    def test_cached_flags_available_for_evaluation(self, mock_get):
+        """Flags loaded from cache are available for local evaluation."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = {
+            "flags": [
+                {
+                    "key": "test-flag",
+                    "active": True,
+                    "filters": {
+                        "groups": [
+                            {
+                                "properties": [],
+                                "rollout_percentage": 100,
+                            }
+                        ]
+                    },
+                }
+            ],
+            "group_type_mapping": {},
+            "cohorts": {},
+        }
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        # Flag should be accessible
+        self.assertEqual(len(client.feature_flags), 1)
+        self.assertEqual(client.feature_flags_by_key["test-flag"]["key"], "test-flag")
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_group_type_mapping_loaded_from_cache(self, mock_get):
+        """Group type mapping is correctly loaded from cache."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = self.sample_flags_data
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        self.assertEqual(client.group_type_mapping["0"], "company")
+        self.assertEqual(client.group_type_mapping["1"], "project")
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_cohorts_loaded_from_cache(self, mock_get):
+        """Cohorts are correctly loaded from cache."""
+        self.cache_provider.should_fetch_return_value = False
+        self.cache_provider.stored_data = self.sample_flags_data
+
+        client = self._create_client_with_cache()
+        client._load_feature_flags()
+
+        self.assertIn("1", client.cohorts)
+
+        client.join()
+
+    @mock.patch("posthog.client.get")
+    def test_cache_updated_when_api_returns_new_data(self, mock_get):
+        """State transition: cache has old data -> API returns new -> cache updated."""
+        # Start with old cached data
+        old_flags_data: FlagDefinitionCacheData = {
+            "flags": [{"key": "old-flag", "active": True, "filters": {}}],
+            "group_type_mapping": {},
+            "cohorts": {},
+        }
+        self.cache_provider.stored_data = old_flags_data
+        self.cache_provider.should_fetch_return_value = False
+
+        client = self._create_client_with_cache()
+
+        # First load from cache
+        client._load_feature_flags()
+        self.assertEqual(client.feature_flags[0]["key"], "old-flag")
+        self.assertEqual(self.cache_provider.on_received_call_count, 0)
+
+        # Now trigger API fetch with new data
+        self.cache_provider.should_fetch_return_value = True
+        new_flags_data: FlagDefinitionCacheData = {
+            "flags": [{"key": "new-flag", "active": True, "filters": {}}],
+            "group_type_mapping": {"0": "company"},
+            "cohorts": {"1": {"properties": []}},
+        }
+        mock_get.return_value = GetResponse(
+            data=new_flags_data, etag="new-etag", not_modified=False
+        )
+
+        client._load_feature_flags()
+
+        # Verify new flags loaded
+        self.assertEqual(client.feature_flags[0]["key"], "new-flag")
+        self.assertEqual(client.group_type_mapping["0"], "company")
+
+        # Verify cache was updated
+        self.assertEqual(self.cache_provider.on_received_call_count, 1)
+        self.assertEqual(self.cache_provider.stored_data["flags"][0]["key"], "new-flag")
+
+        client.join()
+
+
+class TestConcurrency(TestFlagDefinitionCacheProvider):
+    """Tests for thread safety and concurrent access."""
+
+    @mock.patch("posthog.client.get")
+    def test_concurrent_load_feature_flags_is_thread_safe(self, mock_get):
+        """Multiple threads calling _load_feature_flags should not cause errors."""
+        mock_get.return_value = GetResponse(
+            data=self.sample_flags_data, etag="test-etag", not_modified=False
+        )
+
+        client = self._create_client_with_cache()
+        errors = []
+
+        def load_flags():
+            try:
+                client._load_feature_flags()
+            except Exception as e:
+                errors.append(e)
+
+        # Launch 5 threads concurrently
+        threads = [threading.Thread(target=load_flags) for _ in range(5)]
+        for t in threads:
+            t.start()
+        for t in threads:
+            t.join()
+
+        # Should complete without errors
+        self.assertEqual(len(errors), 0, f"Unexpected errors: {errors}")
+
+        # Flags should be loaded
+        self.assertIsNotNone(client.feature_flags)
+        self.assertEqual(len(client.feature_flags), 2)
+
+        client.join()
+
+
+class TestProtocolCompliance(unittest.TestCase):
+    """Tests for Protocol compliance."""
+
+    def test_mock_provider_is_protocol_instance(self):
+        """MockCacheProvider satisfies FlagDefinitionCacheProvider protocol."""
+        provider = MockCacheProvider()
+        self.assertIsInstance(provider, FlagDefinitionCacheProvider)
+
+    def test_incomplete_provider_is_not_protocol_instance(self):
+        """Class missing methods is not a FlagDefinitionCacheProvider."""
+
+        class IncompleteProvider:
+            def get_flag_definitions(self):
+                return None
+
+        provider = IncompleteProvider()
+        self.assertNotIsInstance(provider, FlagDefinitionCacheProvider)
+
+
+if __name__ == "__main__":
+    unittest.main()

posthog/test/test_module.py

@@ -7,31 +7,19 @@ class TestModule(unittest.TestCase):
     posthog = None
 
     def _assert_enqueue_result(self, result):
-        self.assertEqual(type(result[0]), bool)
-        self.assertEqual(type(result[1]), dict)
+        self.assertEqual(type(result[0]), str)
 
     def failed(self):
         self.failed = True
 
     def setUp(self):
         self.failed = False
-        self.posthog = Posthog("testsecret", host="http://localhost:8000", on_error=self.failed)
-
-    def test_no_api_key(self):
-        self.posthog.api_key = None
-        self.assertRaises(Exception, self.posthog.capture)
-
-    def test_no_host(self):
-        self.posthog.host = None
-        self.assertRaises(Exception, self.posthog.capture)
+        self.posthog = Posthog(
+            "testsecret", host="http://localhost:8000", on_error=self.failed
+        )
 
     def test_track(self):
-        res = self.posthog.capture("distinct_id", "python module event")
-        self._assert_enqueue_result(res)
-        self.posthog.flush()
-
-    def test_identify(self):
-        res = self.posthog.identify("distinct_id", {"email": "user@email.com"})
+        res = self.posthog.capture("python module event", distinct_id="distinct_id")
         self._assert_enqueue_result(res)
         self.posthog.flush()
 
@@ -40,9 +28,5 @@ class TestModule(unittest.TestCase):
         self._assert_enqueue_result(res)
         self.posthog.flush()
 
-    def test_page(self):
-        self.posthog.page("distinct_id", "https://posthog.com/contact")
-        self.posthog.flush()
-
     def test_flush(self):
         self.posthog.flush()

posthog/test/test_request.py

@@ -6,20 +6,79 @@ import mock
 import pytest
 import requests
 
-from posthog.request import DatetimeSerializer, QuotaLimitError, batch_post, decide, determine_server_host
+import posthog.request as request_module
+from posthog.request import (
+    APIError,
+    DatetimeSerializer,
+    GetResponse,
+    KEEP_ALIVE_SOCKET_OPTIONS,
+    QuotaLimitError,
+    _mask_tokens_in_url,
+    batch_post,
+    decide,
+    determine_server_host,
+    disable_connection_reuse,
+    enable_keep_alive,
+    flags,
+    get,
+    set_socket_options,
+)
 from posthog.test.test_utils import TEST_API_KEY
 
 
+@pytest.mark.parametrize(
+    "url, expected",
+    [
+        # Token with params after - masks keeping first 10 chars
+        (
+            "https://example.com/api/flags?token=phc_abc123xyz789&send_cohorts",
+            "https://example.com/api/flags?token=phc_abc123...&send_cohorts",
+        ),
+        # Token at end of URL
+        (
+            "https://example.com/api/flags?token=phc_abc123xyz789",
+            "https://example.com/api/flags?token=phc_abc123...",
+        ),
+        # No token - unchanged
+        (
+            "https://example.com/api/flags?other=value",
+            "https://example.com/api/flags?other=value",
+        ),
+        # Short token (<10 chars) - unchanged
+        (
+            "https://example.com/api/flags?token=short",
+            "https://example.com/api/flags?token=short",
+        ),
+        # Exactly 10 char token - gets ellipsis
+        (
+            "https://example.com/api/flags?token=1234567890",
+            "https://example.com/api/flags?token=1234567890...",
+        ),
+    ],
+)
+def test_mask_tokens_in_url(url, expected):
+    assert _mask_tokens_in_url(url) == expected
+
+
 class TestRequests(unittest.TestCase):
     def test_valid_request(self):
-        res = batch_post(TEST_API_KEY, batch=[{"distinct_id": "distinct_id", "event": "python event", "type": "track"}])
+        res = batch_post(
+            TEST_API_KEY,
+            batch=[
+                {"distinct_id": "distinct_id", "event": "python event", "type": "track"}
+            ],
+        )
         self.assertEqual(res.status_code, 200)
 
     def test_invalid_request_error(self):
-        self.assertRaises(Exception, batch_post, "testsecret", "https://t.posthog.com", False, "[{]")
+        self.assertRaises(
+            Exception, batch_post, "testsecret", "https://t.posthog.com", False, "[{]"
+        )
 
     def test_invalid_host(self):
-        self.assertRaises(Exception, batch_post, "testsecret", "t.posthog.com/", batch=[])
+        self.assertRaises(
+            Exception, batch_post, "testsecret", "t.posthog.com/", batch=[]
+        )
 
     def test_datetime_serialization(self):
         data = {"created": datetime(2012, 3, 4, 5, 6, 7, 891011)}
@@ -35,14 +94,26 @@ class TestRequests(unittest.TestCase):
 
     def test_should_not_timeout(self):
         res = batch_post(
-            TEST_API_KEY, batch=[{"distinct_id": "distinct_id", "event": "python event", "type": "track"}], timeout=15
+            TEST_API_KEY,
+            batch=[
+                {"distinct_id": "distinct_id", "event": "python event", "type": "track"}
+            ],
+            timeout=15,
         )
         self.assertEqual(res.status_code, 200)
 
     def test_should_timeout(self):
         with self.assertRaises(requests.ReadTimeout):
             batch_post(
-                "key", batch=[{"distinct_id": "distinct_id", "event": "python event", "type": "track"}], timeout=0.0001
+                "key",
+                batch=[
+                    {
+                        "distinct_id": "distinct_id",
+                        "event": "python event",
+                        "type": "track",
+                    }
+                ],
+                timeout=0.0001,
             )
 
     def test_quota_limited_response(self):
@@ -68,7 +139,11 @@ class TestRequests(unittest.TestCase):
         mock_response = requests.Response()
         mock_response.status_code = 200
         mock_response._content = json.dumps(
-            {"featureFlags": {"flag1": True}, "featureFlagPayloads": {}, "errorsWhileComputingFlags": False}
+            {
+                "featureFlags": {"flag1": True},
+                "featureFlagPayloads": {},
+                "errorsWhileComputingFlags": False,
+            }
         ).encode("utf-8")
 
         with mock.patch("posthog.request._session.post", return_value=mock_response):
@@ -76,6 +151,184 @@ class TestRequests(unittest.TestCase):
             self.assertEqual(response["featureFlags"], {"flag1": True})
 
 
+class TestGet(unittest.TestCase):
+    """Unit tests for the get() function HTTP-level behavior."""
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_returns_data_and_etag(self, mock_get):
+        """Test that get() returns GetResponse with data and etag from headers."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response.headers["ETag"] = '"abc123"'
+        mock_response._content = json.dumps({"flags": [{"key": "test-flag"}]}).encode(
+            "utf-8"
+        )
+        mock_get.return_value = mock_response
+
+        response = get("api_key", "/test-url", host="https://example.com")
+
+        self.assertIsInstance(response, GetResponse)
+        self.assertEqual(response.data, {"flags": [{"key": "test-flag"}]})
+        self.assertEqual(response.etag, '"abc123"')
+        self.assertFalse(response.not_modified)
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_sends_if_none_match_header_when_etag_provided(self, mock_get):
+        """Test that If-None-Match header is sent when etag parameter is provided."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response.headers["ETag"] = '"new-etag"'
+        mock_response._content = json.dumps({"flags": []}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/test-url", host="https://example.com", etag='"previous-etag"')
+
+        call_kwargs = mock_get.call_args[1]
+        self.assertEqual(call_kwargs["headers"]["If-None-Match"], '"previous-etag"')
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_does_not_send_if_none_match_when_no_etag(self, mock_get):
+        """Test that If-None-Match header is not sent when no etag provided."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({"flags": []}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/test-url", host="https://example.com")
+
+        call_kwargs = mock_get.call_args[1]
+        self.assertNotIn("If-None-Match", call_kwargs["headers"])
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_handles_304_not_modified(self, mock_get):
+        """Test that 304 Not Modified response returns not_modified=True with no data."""
+        mock_response = requests.Response()
+        mock_response.status_code = 304
+        mock_response.headers["ETag"] = '"unchanged-etag"'
+        mock_get.return_value = mock_response
+
+        response = get(
+            "api_key", "/test-url", host="https://example.com", etag='"unchanged-etag"'
+        )
+
+        self.assertIsInstance(response, GetResponse)
+        self.assertIsNone(response.data)
+        self.assertEqual(response.etag, '"unchanged-etag"')
+        self.assertTrue(response.not_modified)
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_304_without_etag_header_uses_request_etag(self, mock_get):
+        """Test that 304 response without ETag header falls back to request etag."""
+        mock_response = requests.Response()
+        mock_response.status_code = 304
+        # Server doesn't return ETag header on 304
+        mock_get.return_value = mock_response
+
+        response = get(
+            "api_key", "/test-url", host="https://example.com", etag='"original-etag"'
+        )
+
+        self.assertTrue(response.not_modified)
+        self.assertEqual(response.etag, '"original-etag"')
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_200_without_etag_header(self, mock_get):
+        """Test that 200 response without ETag header returns None for etag."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({"flags": []}).encode("utf-8")
+        # No ETag header
+        mock_get.return_value = mock_response
+
+        response = get("api_key", "/test-url", host="https://example.com")
+
+        self.assertFalse(response.not_modified)
+        self.assertIsNone(response.etag)
+        self.assertEqual(response.data, {"flags": []})
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_error_response_raises_api_error(self, mock_get):
+        """Test that error responses raise APIError."""
+        mock_response = requests.Response()
+        mock_response.status_code = 401
+        mock_response._content = json.dumps({"detail": "Unauthorized"}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        with self.assertRaises(APIError) as ctx:
+            get("bad_key", "/test-url", host="https://example.com")
+
+        self.assertEqual(ctx.exception.status, 401)
+        self.assertEqual(ctx.exception.message, "Unauthorized")
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_sends_authorization_header(self, mock_get):
+        """Test that Authorization header is sent with Bearer token."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("my-api-key", "/test-url", host="https://example.com")
+
+        call_kwargs = mock_get.call_args[1]
+        self.assertEqual(call_kwargs["headers"]["Authorization"], "Bearer my-api-key")
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_sends_user_agent_header(self, mock_get):
+        """Test that User-Agent header is sent."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/test-url", host="https://example.com")
+
+        call_kwargs = mock_get.call_args[1]
+        self.assertIn("User-Agent", call_kwargs["headers"])
+        self.assertTrue(
+            call_kwargs["headers"]["User-Agent"].startswith("posthog-python/")
+        )
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_passes_timeout(self, mock_get):
+        """Test that timeout parameter is passed to the request."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/test-url", host="https://example.com", timeout=30)
+
+        call_kwargs = mock_get.call_args[1]
+        self.assertEqual(call_kwargs["timeout"], 30)
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_constructs_full_url(self, mock_get):
+        """Test that host and url are combined correctly."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/api/flags", host="https://example.com")
+
+        call_args = mock_get.call_args[0]
+        self.assertEqual(call_args[0], "https://example.com/api/flags")
+
+    @mock.patch("posthog.request._session.get")
+    def test_get_removes_trailing_slash_from_host(self, mock_get):
+        """Test that trailing slash is removed from host."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps({}).encode("utf-8")
+        mock_get.return_value = mock_response
+
+        get("api_key", "/api/flags", host="https://example.com/")
+
+        call_args = mock_get.call_args[0]
+        self.assertEqual(call_args[0], "https://example.com/api/flags")
+
+
 @pytest.mark.parametrize(
     "host, expected",
     [
@@ -97,3 +350,317 @@ class TestRequests(unittest.TestCase):
 )
 def test_routing_to_custom_host(host, expected):
     assert determine_server_host(host) == expected
+
+
+def test_enable_keep_alive_sets_socket_options():
+    try:
+        enable_keep_alive()
+        from posthog.request import _session
+
+        adapter = _session.get_adapter("https://example.com")
+        assert adapter.socket_options == KEEP_ALIVE_SOCKET_OPTIONS
+    finally:
+        set_socket_options(None)
+
+
+def test_set_socket_options_clears_with_none():
+    try:
+        enable_keep_alive()
+        set_socket_options(None)
+        from posthog.request import _session
+
+        adapter = _session.get_adapter("https://example.com")
+        assert adapter.socket_options is None
+    finally:
+        set_socket_options(None)
+
+
+def test_disable_connection_reuse_creates_fresh_sessions():
+    try:
+        disable_connection_reuse()
+        session1 = request_module._get_session()
+        session2 = request_module._get_session()
+        assert session1 is not session2
+    finally:
+        request_module._pooling_enabled = True
+
+
+def test_set_socket_options_is_idempotent():
+    try:
+        enable_keep_alive()
+        session1 = request_module._session
+        enable_keep_alive()
+        session2 = request_module._session
+        assert session1 is session2
+    finally:
+        set_socket_options(None)
+
+
+class TestFlagsSession(unittest.TestCase):
+    """Tests for flags session configuration."""
+
+    def test_retry_status_forcelist_excludes_rate_limits(self):
+        """Verify 429 (rate limit) is NOT retried - need to wait, not hammer."""
+        from posthog.request import RETRY_STATUS_FORCELIST
+
+        self.assertNotIn(429, RETRY_STATUS_FORCELIST)
+
+    def test_retry_status_forcelist_excludes_quota_errors(self):
+        """Verify 402 (payment required/quota) is NOT retried - won't resolve."""
+        from posthog.request import RETRY_STATUS_FORCELIST
+
+        self.assertNotIn(402, RETRY_STATUS_FORCELIST)
+
+    @mock.patch("posthog.request._get_flags_session")
+    def test_flags_uses_flags_session(self, mock_get_flags_session):
+        """flags() uses the dedicated flags session, not the general session."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps(
+            {
+                "featureFlags": {"test-flag": True},
+                "featureFlagPayloads": {},
+                "errorsWhileComputingFlags": False,
+            }
+        ).encode("utf-8")
+
+        mock_session = mock.MagicMock()
+        mock_session.post.return_value = mock_response
+        mock_get_flags_session.return_value = mock_session
+
+        result = flags("test-key", "https://test.posthog.com", distinct_id="user123")
+
+        self.assertEqual(result["featureFlags"]["test-flag"], True)
+        mock_get_flags_session.assert_called_once()
+        mock_session.post.assert_called_once()
+
+    @mock.patch("posthog.request._get_flags_session")
+    def test_flags_no_retry_on_quota_limit(self, mock_get_flags_session):
+        """flags() raises QuotaLimitError without retrying (at application level)."""
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps(
+            {
+                "quotaLimited": ["feature_flags"],
+                "featureFlags": {},
+                "featureFlagPayloads": {},
+                "errorsWhileComputingFlags": False,
+            }
+        ).encode("utf-8")
+
+        mock_session = mock.MagicMock()
+        mock_session.post.return_value = mock_response
+        mock_get_flags_session.return_value = mock_session
+
+        with self.assertRaises(QuotaLimitError):
+            flags("test-key", "https://test.posthog.com", distinct_id="user123")
+
+        # QuotaLimitError is raised after response is received, not retried
+        self.assertEqual(mock_session.post.call_count, 1)
+
+
+class TestFlagsSessionNetworkRetries(unittest.TestCase):
+    """Tests for network failure retries in the flags session."""
+
+    def test_flags_session_retry_config_includes_connection_errors(self):
+        """
+        Verify that the flags session is configured to retry on connection errors.
+
+        The urllib3 Retry adapter with connect=2 and read=2 automatically
+        retries on network-level failures (DNS failures, connection refused,
+        connection reset, etc.) up to 2 times each.
+        """
+        from posthog.request import _build_flags_session
+
+        session = _build_flags_session()
+
+        # Get the adapter for https://
+        adapter = session.get_adapter("https://test.posthog.com")
+
+        # Verify retry configuration
+        retry = adapter.max_retries
+        self.assertEqual(retry.total, 2, "Should have 2 total retries")
+        self.assertEqual(retry.connect, 2, "Should retry connection errors twice")
+        self.assertEqual(retry.read, 2, "Should retry read errors twice")
+        self.assertIn("POST", retry.allowed_methods, "Should allow POST retries")
+
+    def test_flags_session_retries_on_server_errors(self):
+        """
+        Verify that transient server errors (5xx) trigger retries.
+
+        This tests the status_forcelist configuration which specifies
+        which HTTP status codes should trigger a retry.
+        """
+        from posthog.request import _build_flags_session, RETRY_STATUS_FORCELIST
+
+        session = _build_flags_session()
+        adapter = session.get_adapter("https://test.posthog.com")
+        retry = adapter.max_retries
+
+        # Verify the status codes that trigger retries
+        self.assertEqual(
+            set(retry.status_forcelist),
+            set(RETRY_STATUS_FORCELIST),
+            "Should retry on transient server errors",
+        )
+
+        # Verify specific codes are included
+        self.assertIn(500, retry.status_forcelist)
+        self.assertIn(502, retry.status_forcelist)
+        self.assertIn(503, retry.status_forcelist)
+        self.assertIn(504, retry.status_forcelist)
+
+        # Verify rate limits and quota errors are NOT retried
+        self.assertNotIn(429, retry.status_forcelist)
+        self.assertNotIn(402, retry.status_forcelist)
+
+    def test_flags_session_has_backoff(self):
+        """
+        Verify that retries use exponential backoff to avoid thundering herd.
+        """
+        from posthog.request import _build_flags_session
+
+        session = _build_flags_session()
+        adapter = session.get_adapter("https://test.posthog.com")
+        retry = adapter.max_retries
+
+        self.assertEqual(
+            retry.backoff_factor,
+            0.5,
+            "Should use 0.5s backoff factor (0.5s, 1s delays)",
+        )
+
+
+class TestFlagsSessionRetryIntegration(unittest.TestCase):
+    """Integration tests that verify actual retry behavior with a local server."""
+
+    def test_retries_on_503_then_succeeds(self):
+        """
+        Verify that 503 errors trigger retries and eventually succeed.
+
+        Uses a local HTTP server that fails twice with 503, then succeeds.
+        This tests the full retry flow including backoff timing.
+        """
+        import threading
+        from http.server import HTTPServer, BaseHTTPRequestHandler
+        from socketserver import ThreadingMixIn
+        from urllib3.util.retry import Retry
+        from posthog.request import HTTPAdapterWithSocketOptions, RETRY_STATUS_FORCELIST
+
+        request_count = 0
+
+        class RetryTestHandler(BaseHTTPRequestHandler):
+            protocol_version = "HTTP/1.1"
+
+            def do_POST(self):
+                nonlocal request_count
+                request_count += 1
+
+                # Read and discard request body to prevent connection issues
+                content_length = int(self.headers.get("Content-Length", 0))
+                if content_length > 0:
+                    self.rfile.read(content_length)
+
+                if request_count <= 2:
+                    self.send_response(503)
+                    self.send_header("Content-Type", "application/json")
+                    body = b'{"error": "Service unavailable"}'
+                    self.send_header("Content-Length", str(len(body)))
+                    self.end_headers()
+                    self.wfile.write(body)
+                else:
+                    self.send_response(200)
+                    self.send_header("Content-Type", "application/json")
+                    body = (
+                        b'{"featureFlags": {"test": true}, "featureFlagPayloads": {}}'
+                    )
+                    self.send_header("Content-Length", str(len(body)))
+                    self.end_headers()
+                    self.wfile.write(body)
+
+            def log_message(self, format, *args):
+                pass  # Suppress logging
+
+        # Use ThreadingMixIn for cleaner shutdown
+        class ThreadedHTTPServer(ThreadingMixIn, HTTPServer):
+            daemon_threads = True
+
+        # Start server on a random available port
+        server = ThreadedHTTPServer(("127.0.0.1", 0), RetryTestHandler)
+        port = server.server_address[1]
+        server_thread = threading.Thread(target=server.serve_forever)
+        server_thread.daemon = True
+        server_thread.start()
+
+        try:
+            # Build session with same retry config as _build_flags_session
+            # but mounted on http:// for local testing
+            adapter = HTTPAdapterWithSocketOptions(
+                max_retries=Retry(
+                    total=2,
+                    connect=2,
+                    read=2,
+                    backoff_factor=0.01,  # Fast backoff for testing
+                    status_forcelist=RETRY_STATUS_FORCELIST,
+                    allowed_methods=["POST"],
+                ),
+            )
+            session = requests.Session()
+            session.mount("http://", adapter)
+
+            response = session.post(
+                f"http://127.0.0.1:{port}/flags/?v=2",
+                json={"distinct_id": "user123"},
+                timeout=5,
+            )
+
+            # Should succeed on 3rd attempt
+            self.assertEqual(response.status_code, 200)
+            self.assertEqual(request_count, 3)  # 1 initial + 2 retries
+        finally:
+            server.shutdown()
+            server.server_close()
+
+    def test_connection_errors_are_retried(self):
+        """
+        Verify that connection errors (no server) trigger retries.
+
+        Binds a socket to get a guaranteed available port, then closes it
+        so connection attempts fail with ConnectionError.
+        """
+        import socket
+        import time
+        from urllib3.util.retry import Retry
+        from posthog.request import HTTPAdapterWithSocketOptions, RETRY_STATUS_FORCELIST
+
+        # Get an available port by binding then closing a socket
+        sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+        sock.bind(("127.0.0.1", 0))
+        port = sock.getsockname()[1]
+        sock.close()  # Port is now available but nothing is listening
+
+        adapter = HTTPAdapterWithSocketOptions(
+            max_retries=Retry(
+                total=2,
+                connect=2,
+                read=2,
+                backoff_factor=0.05,  # Very fast for testing
+                status_forcelist=RETRY_STATUS_FORCELIST,
+                allowed_methods=["POST"],
+            ),
+        )
+        session = requests.Session()
+        session.mount("http://", adapter)
+
+        start = time.time()
+        with self.assertRaises(requests.exceptions.ConnectionError):
+            session.post(
+                f"http://127.0.0.1:{port}/flags/?v=2",
+                json={"distinct_id": "user123"},
+                timeout=1,
+            )
+        elapsed = time.time() - start
+
+        # With 3 attempts and backoff, should take more than instant
+        # but less than timeout (confirms retries happened)
+        self.assertGreater(elapsed, 0.05, "Should have some delay from retries")

posthog/test/test_size_limited_dict.py

@@ -0,0 +1,24 @@
+import unittest
+
+from parameterized import parameterized
+
+from posthog import utils
+
+
+class TestSizeLimitedDict(unittest.TestCase):
+    @parameterized.expand([(10, 100), (5, 20), (20, 200)])
+    def test_size_limited_dict(self, size: int, iterations: int) -> None:
+        values = utils.SizeLimitedDict(size, lambda _: -1)
+
+        for i in range(iterations):
+            values[i] = i
+
+            assert values[i] == i
+            assert len(values) == i % size + 1
+
+            if i % size == 0:
+                # old numbers should've been removed
+                self.assertIsNone(values.get(i - 1))
+                self.assertIsNone(values.get(i - 3))
+                self.assertIsNone(values.get(i - 5))
+                self.assertIsNone(values.get(i - 9))

posthog/test/test_types.py

@@ -22,9 +22,16 @@ class TestTypes(unittest.TestCase):
                     enabled=True,
                     variant="test-variant",
                     reason=FlagReason(
-                        code="matched_condition", condition_index=0, description="Matched condition set 1"
+                        code="matched_condition",
+                        condition_index=0,
+                        description="Matched condition set 1",
+                    ),
+                    metadata=FlagMetadata(
+                        id=1,
+                        payload='{"some": "json"}',
+                        version=2,
+                        description="test-description",
                     ),
-                    metadata=FlagMetadata(id=1, payload='{"some": "json"}', version=2, description="test-description"),
                 )
             },
             "errorsWhileComputingFlags": has_errors,
@@ -39,10 +46,21 @@ class TestTypes(unittest.TestCase):
         self.assertEqual(flag.variant, "test-variant")
         self.assertEqual(flag.get_value(), "test-variant")
         self.assertEqual(
-            flag.reason, FlagReason(code="matched_condition", condition_index=0, description="Matched condition set 1")
+            flag.reason,
+            FlagReason(
+                code="matched_condition",
+                condition_index=0,
+                description="Matched condition set 1",
+            ),
         )
         self.assertEqual(
-            flag.metadata, FlagMetadata(id=1, payload='{"some": "json"}', version=2, description="test-description")
+            flag.metadata,
+            FlagMetadata(
+                id=1,
+                payload='{"some": "json"}',
+                version=2,
+                description="test-description",
+            ),
         )
         self.assertEqual(result["errorsWhileComputingFlags"], has_errors)
         self.assertEqual(result["requestId"], "test-id")
@@ -64,7 +82,9 @@ class TestTypes(unittest.TestCase):
         self.assertEqual(flag.variant, "test-variant")
         self.assertEqual(flag.get_value(), "test-variant")
         self.assertIsNone(flag.reason)
-        self.assertEqual(flag.metadata, LegacyFlagMetadata(payload='{"some": "json-payload"}'))
+        self.assertEqual(
+            flag.metadata, LegacyFlagMetadata(payload='{"some": "json-payload"}')
+        )
         self.assertFalse(result["errorsWhileComputingFlags"])
         self.assertEqual(result["requestId"], "test-id")
         # Verify legacy fields are removed
@@ -99,18 +119,29 @@ class TestTypes(unittest.TestCase):
                     enabled=True,
                     variant="test-variant",
                     reason=FlagReason(
-                        code="matched_condition", condition_index=0, description="Matched condition set 1"
+                        code="matched_condition",
+                        condition_index=0,
+                        description="Matched condition set 1",
+                    ),
+                    metadata=FlagMetadata(
+                        id=1,
+                        payload='{"some": "json"}',
+                        version=2,
+                        description="test-description",
                     ),
-                    metadata=FlagMetadata(id=1, payload='{"some": "json"}', version=2, description="test-description"),
                 ),
                 "my-boolean-flag": FeatureFlag(
                     key="my-boolean-flag",
                     enabled=True,
                     variant=None,
                     reason=FlagReason(
-                        code="matched_condition", condition_index=0, description="Matched condition set 1"
+                        code="matched_condition",
+                        condition_index=0,
+                        description="Matched condition set 1",
+                    ),
+                    metadata=FlagMetadata(
+                        id=1, payload=None, version=2, description="test-description"
                     ),
-                    metadata=FlagMetadata(id=1, payload=None, version=2, description="test-description"),
                 ),
                 "disabled-flag": FeatureFlag(
                     key="disabled-flag",
@@ -129,7 +160,9 @@ class TestTypes(unittest.TestCase):
         self.assertEqual(result["featureFlags"]["my-variant-flag"], "test-variant")
         self.assertEqual(result["featureFlags"]["my-boolean-flag"], True)
         self.assertEqual(result["featureFlags"]["disabled-flag"], False)
-        self.assertEqual(result["featureFlagPayloads"]["my-variant-flag"], '{"some": "json"}')
+        self.assertEqual(
+            result["featureFlagPayloads"]["my-variant-flag"], '{"some": "json"}'
+        )
         self.assertNotIn("my-boolean-flag", result["featureFlagPayloads"])
         self.assertNotIn("disabled-flag", result["featureFlagPayloads"])
 

posthog/test/test_utils.py

@@ -1,3 +1,5 @@
+import sys
+import time
 import unittest
 from dataclasses import dataclass
 from datetime import date, datetime, timedelta
@@ -7,27 +9,41 @@ from uuid import UUID
 
 import six
 from dateutil.tz import tzutc
+from parameterized import parameterized
 from pydantic import BaseModel
 from pydantic.v1 import BaseModel as BaseModelV1
 
 from posthog import utils
+from posthog.types import FeatureFlagResult
 
 TEST_API_KEY = "kOOlRy2QlMY9jHZQv0bKz0FZyazBUoY8Arj0lFVNjs4"
 FAKE_TEST_API_KEY = "random_key"
 
 
 class TestUtils(unittest.TestCase):
+    @parameterized.expand(
+        [
+            ("naive datetime should be naive", True),
+            ("timezone-aware datetime should not be naive", False),
+        ]
+    )
+    def test_is_naive(self, _name: str, expected_naive: bool):
+        if expected_naive:
+            dt = datetime.now()  # naive datetime
+        else:
+            dt = datetime.now(tz=tzutc())  # timezone-aware datetime
+
+        assert utils.is_naive(dt) is expected_naive
+
     def test_timezone_utils(self):
         now = datetime.now()
         utcnow = datetime.now(tz=tzutc())
-        self.assertTrue(utils.is_naive(now))
-        self.assertFalse(utils.is_naive(utcnow))
 
         fixed = utils.guess_timezone(now)
-        self.assertFalse(utils.is_naive(fixed))
+        assert utils.is_naive(fixed) is False
 
         shouldnt_be_edited = utils.guess_timezone(utcnow)
-        self.assertEqual(utcnow, shouldnt_be_edited)
+        assert utcnow == shouldnt_be_edited
 
     def test_clean(self):
         simple = {
@@ -54,12 +70,12 @@ class TestUtils(unittest.TestCase):
         pre_clean_keys = combined.keys()
 
         utils.clean(combined)
-        self.assertEqual(combined.keys(), pre_clean_keys)
+        assert combined.keys() == pre_clean_keys
 
         # test UUID separately, as the UUID object doesn't equal its string representation according to Python
-        self.assertEqual(
-            utils.clean(UUID("12345678123456781234567812345678")),
-            "12345678-1234-5678-1234-567812345678",
+        assert (
+            utils.clean(UUID("12345678123456781234567812345678"))
+            == "12345678-1234-5678-1234-567812345678"
         )
 
     def test_clean_with_dates(self):
@@ -67,26 +83,27 @@ class TestUtils(unittest.TestCase):
             "birthdate": date(1980, 1, 1),
             "registration": datetime.now(tz=tzutc()),
         }
-        self.assertEqual(dict_with_dates, utils.clean(dict_with_dates))
+        assert dict_with_dates == utils.clean(dict_with_dates)
 
     def test_bytes(self):
-        if six.PY3:
-            item = bytes(10)
-        else:
-            item = bytearray(10)
-
+        item = bytes(10)
         utils.clean(item)
+        assert utils.clean(item) == "\x00\x00\x00\x00\x00\x00\x00\x00\x00\x00"
 
     def test_clean_fn(self):
         cleaned = utils.clean({"fn": lambda x: x, "number": 4})
-        self.assertEqual(cleaned["number"], 4)
-        # TODO: fixme, different behavior on python 2 and 3
-        if "fn" in cleaned:
-            self.assertEqual(cleaned["fn"], None)
+        assert cleaned == {"fn": None, "number": 4}
 
-    def test_remove_slash(self):
-        self.assertEqual("http://posthog.io", utils.remove_trailing_slash("http://posthog.io/"))
-        self.assertEqual("http://posthog.io", utils.remove_trailing_slash("http://posthog.io"))
+    @parameterized.expand(
+        [
+            ("http://posthog.io/", "http://posthog.io"),
+            ("http://posthog.io", "http://posthog.io"),
+            ("https://example.com/path/", "https://example.com/path"),
+            ("https://example.com/path", "https://example.com/path"),
+        ]
+    )
+    def test_remove_slash(self, input_url, expected_url):
+        assert expected_url == utils.remove_trailing_slash(input_url)
 
     def test_clean_pydantic(self):
         class ModelV2(BaseModel):
@@ -101,19 +118,28 @@ class TestUtils(unittest.TestCase):
         class NestedModel(BaseModel):
             foo: ModelV2
 
-        self.assertEqual(utils.clean(ModelV2(foo="1", bar=2)), {"foo": "1", "bar": 2, "baz": None})
-        self.assertEqual(utils.clean(ModelV1(foo=1, bar="2")), {"foo": 1, "bar": "2"})
-        self.assertEqual(
-            utils.clean(NestedModel(foo=ModelV2(foo="1", bar=2, baz="3"))),
-            {"foo": {"foo": "1", "bar": 2, "baz": "3"}},
-        )
+        assert utils.clean(ModelV2(foo="1", bar=2)) == {
+            "foo": "1",
+            "bar": 2,
+            "baz": None,
+        }
+        # Pydantic V1 is not compatible with Python 3.14+
+        if sys.version_info < (3, 14):
+            assert utils.clean(ModelV1(foo=1, bar="2")) == {"foo": 1, "bar": "2"}
+        assert utils.clean(NestedModel(foo=ModelV2(foo="1", bar=2, baz="3"))) == {
+            "foo": {"foo": "1", "bar": 2, "baz": "3"}
+        }
 
+    def test_clean_pydantic_like_class(self) -> None:
         class Dummy:
-            def model_dump(self, required_param):
-                pass
+            def model_dump(self, required_param: str) -> dict:
+                return {}
 
-        # Skips a class with a defined non-Pydantic `model_dump` method.
-        self.assertEqual(utils.clean({"test": Dummy()}), {})
+        # previously python 2 code would cause an error while cleaning,
+        # and this entire object would be None, and we would log an error
+        # let's allow ourselves to clean `Dummy` as None,
+        # without blatting the `test` key
+        assert utils.clean({"test": Dummy()}) == {"test": None}
 
     def test_clean_dataclass(self):
         @dataclass
@@ -130,47 +156,146 @@ class TestUtils(unittest.TestCase):
             bar: int
             nested: InnerDataClass
 
-        self.assertEqual(
-            utils.clean(
-                TestDataClass(
-                    foo="1",
-                    bar=2,
-                    nested=InnerDataClass(
-                        inner_foo="3",
-                        inner_bar=4,
-                        inner_uuid=UUID("12345678123456781234567812345678"),
-                        inner_date=datetime(2025, 1, 1),
-                    ),
-                )
-            ),
-            {
-                "foo": "1",
-                "bar": 2,
-                "nested": {
-                    "inner_foo": "3",
-                    "inner_bar": 4,
-                    "inner_uuid": "12345678-1234-5678-1234-567812345678",
-                    "inner_date": datetime(2025, 1, 1),
-                    "inner_optional": None,
-                },
+        assert utils.clean(
+            TestDataClass(
+                foo="1",
+                bar=2,
+                nested=InnerDataClass(
+                    inner_foo="3",
+                    inner_bar=4,
+                    inner_uuid=UUID("12345678123456781234567812345678"),
+                    inner_date=datetime(2025, 1, 1),
+                ),
+            )
+        ) == {
+            "foo": "1",
+            "bar": 2,
+            "nested": {
+                "inner_foo": "3",
+                "inner_bar": 4,
+                "inner_uuid": "12345678-1234-5678-1234-567812345678",
+                "inner_date": datetime(2025, 1, 1),
+                "inner_optional": None,
             },
+        }
+
+
+class TestFlagCache(unittest.TestCase):
+    def setUp(self):
+        self.cache = utils.FlagCache(max_size=3, default_ttl=1)
+        self.flag_result = FeatureFlagResult.from_value_and_payload(
+            "test-flag", True, None
         )
 
+    def test_cache_basic_operations(self):
+        distinct_id = "user123"
+        flag_key = "test-flag"
+        flag_version = 1
 
-class TestSizeLimitedDict(unittest.TestCase):
-    def test_size_limited_dict(self):
-        size = 10
-        values = utils.SizeLimitedDict(size, lambda _: -1)
+        # Test cache miss
+        result = self.cache.get_cached_flag(distinct_id, flag_key, flag_version)
+        assert result is None
 
-        for i in range(100):
-            values[i] = i
+        # Test cache set and hit
+        self.cache.set_cached_flag(
+            distinct_id, flag_key, self.flag_result, flag_version
+        )
+        result = self.cache.get_cached_flag(distinct_id, flag_key, flag_version)
+        assert result is not None
+        assert result.get_value()
 
-            self.assertEqual(values[i], i)
-            self.assertEqual(len(values), i % size + 1)
+    def test_cache_ttl_expiration(self):
+        distinct_id = "user123"
+        flag_key = "test-flag"
+        flag_version = 1
 
-            if i % size == 0:
-                # old numbers should've been removed
-                self.assertIsNone(values.get(i - 1))
-                self.assertIsNone(values.get(i - 3))
-                self.assertIsNone(values.get(i - 5))
-                self.assertIsNone(values.get(i - 9))
+        # Set flag in cache
+        self.cache.set_cached_flag(
+            distinct_id, flag_key, self.flag_result, flag_version
+        )
+
+        # Should be available immediately
+        result = self.cache.get_cached_flag(distinct_id, flag_key, flag_version)
+        assert result is not None
+
+        # Wait for TTL to expire (1 second + buffer)
+        time.sleep(1.1)
+
+        # Should be expired
+        result = self.cache.get_cached_flag(distinct_id, flag_key, flag_version)
+        assert result is None
+
+    def test_cache_version_invalidation(self):
+        distinct_id = "user123"
+        flag_key = "test-flag"
+        old_version = 1
+        new_version = 2
+
+        # Set flag with old version
+        self.cache.set_cached_flag(distinct_id, flag_key, self.flag_result, old_version)
+
+        # Should hit with old version
+        result = self.cache.get_cached_flag(distinct_id, flag_key, old_version)
+        assert result is not None
+
+        # Should miss with new version
+        result = self.cache.get_cached_flag(distinct_id, flag_key, new_version)
+        assert result is None
+
+        # Invalidate old version
+        self.cache.invalidate_version(old_version)
+
+        # Should miss even with old version after invalidation
+        result = self.cache.get_cached_flag(distinct_id, flag_key, old_version)
+        assert result is None
+
+    def test_stale_cache_functionality(self):
+        distinct_id = "user123"
+        flag_key = "test-flag"
+        flag_version = 1
+
+        # Set flag in cache
+        self.cache.set_cached_flag(
+            distinct_id, flag_key, self.flag_result, flag_version
+        )
+
+        # Wait for TTL to expire
+        time.sleep(1.1)
+
+        # Should not get fresh cache
+        result = self.cache.get_cached_flag(distinct_id, flag_key, flag_version)
+        assert result is None
+
+        # Should get stale cache (within 1 hour default)
+        stale_result = self.cache.get_stale_cached_flag(distinct_id, flag_key)
+        assert stale_result is not None
+        assert stale_result.get_value()
+
+    def test_lru_eviction(self):
+        # Cache has max_size=3, so adding 4 users should evict the LRU one
+        flag_version = 1
+
+        # Add 3 users
+        for i in range(3):
+            user_id = f"user{i}"
+            self.cache.set_cached_flag(
+                user_id, "test-flag", self.flag_result, flag_version
+            )
+
+        # Access user0 to make it recently used
+        self.cache.get_cached_flag("user0", "test-flag", flag_version)
+
+        # Add 4th user, should evict user1 (least recently used)
+        self.cache.set_cached_flag("user3", "test-flag", self.flag_result, flag_version)
+
+        # user0 should still be there (was recently accessed)
+        result = self.cache.get_cached_flag("user0", "test-flag", flag_version)
+        assert result is not None
+
+        # user2 should still be there (was recently added)
+        result = self.cache.get_cached_flag("user2", "test-flag", flag_version)
+        assert result is not None
+
+        # user3 should be there (just added)
+        result = self.cache.get_cached_flag("user3", "test-flag", flag_version)
+        assert result is not None

posthog/types.py

@@ -1,9 +1,34 @@
 import json
 from dataclasses import dataclass
-from typing import Any, List, Optional, TypedDict, Union, cast
+from typing import Any, Callable, List, Optional, TypedDict, Union, cast
 
 FlagValue = Union[bool, str]
 
+# Type alias for the before_send callback function
+# Takes an event dictionary and returns the modified event or None to drop it
+BeforeSendCallback = Callable[[dict[str, Any]], Optional[dict[str, Any]]]
+
+
+# Type alias for the send_feature_flags parameter
+class SendFeatureFlagsOptions(TypedDict, total=False):
+    """Options for sending feature flags with capture events.
+
+    Args:
+        only_evaluate_locally: Whether to only use local evaluation for feature flags.
+            If True, only flags that can be evaluated locally will be included.
+            If False, remote evaluation via /flags API will be used when needed.
+        person_properties: Properties to use for feature flag evaluation specific to this event.
+            These properties will be merged with any existing person properties.
+        group_properties: Group properties to use for feature flag evaluation specific to this event.
+            Format: { group_type_name: { group_properties } }
+    """
+
+    should_send: bool
+    only_evaluate_locally: Optional[bool]
+    person_properties: Optional[dict[str, Any]]
+    group_properties: Optional[dict[str, dict[str, Any]]]
+    flag_keys_filter: Optional[list[str]]
+
 
 @dataclass(frozen=True)
 class FlagReason:
@@ -78,7 +103,9 @@ class FeatureFlag:
         )
 
     @classmethod
-    def from_value_and_payload(cls, key: str, value: FlagValue, payload: Any) -> "FeatureFlag":
+    def from_value_and_payload(
+        cls, key: str, value: FlagValue, payload: Any
+    ) -> "FeatureFlag":
         enabled, variant = (True, value) if isinstance(value, str) else (value, None)
         return cls(
             key=key,
@@ -86,7 +113,7 @@ class FeatureFlag:
             variant=variant,
             reason=None,
             metadata=LegacyFlagMetadata(
-                payload=payload if payload else None,
+                payload=payload,
             ),
         )
 
@@ -96,6 +123,7 @@ class FlagsResponse(TypedDict, total=False):
     errorsWhileComputingFlags: bool
     requestId: str
     quotaLimit: Optional[List[str]]
+    evaluatedAt: Optional[int]
 
 
 class FlagsAndPayloads(TypedDict, total=True):
@@ -154,13 +182,17 @@ class FeatureFlagResult:
             key=key,
             enabled=enabled,
             variant=variant,
-            payload=json.loads(payload) if isinstance(payload, str) else payload,
+            payload=json.loads(payload)
+            if isinstance(payload, str) and payload
+            else payload,
             reason=None,
         )
 
     @classmethod
     def from_flag_details(
-        cls, details: Union[FeatureFlag, None], override_match_value: Optional[FlagValue] = None
+        cls,
+        details: Union[FeatureFlag, None],
+        override_match_value: Optional[FlagValue] = None,
     ) -> "FeatureFlagResult | None":
         """
         Create a FeatureFlagResult from a FeatureFlag object.
@@ -179,7 +211,9 @@ class FeatureFlagResult:
 
         if override_match_value is not None:
             enabled, variant = (
-                (True, override_match_value) if isinstance(override_match_value, str) else (override_match_value, None)
+                (True, override_match_value)
+                if isinstance(override_match_value, str)
+                else (override_match_value, None)
             )
         else:
             enabled, variant = (details.enabled, details.variant)
@@ -191,6 +225,7 @@ class FeatureFlagResult:
             payload=(
                 json.loads(details.metadata.payload)
                 if isinstance(details.metadata.payload, str)
+                and details.metadata.payload
                 else details.metadata.payload
             ),
             reason=details.reason.description if details.reason else None,
@@ -226,7 +261,9 @@ def normalize_flags_response(resp: Any) -> FlagsResponse:
         # look at each key in featureFlags and create a FeatureFlag object
         flags = {}
         for key, value in featureFlags.items():
-            flags[key] = FeatureFlag.from_value_and_payload(key, value, featureFlagPayloads.get(key, None))
+            flags[key] = FeatureFlag.from_value_and_payload(
+                key, value, featureFlagPayloads.get(key, None)
+            )
         resp["flags"] = flags
     return cast(FlagsResponse, resp)
 
@@ -252,7 +289,11 @@ def to_values(response: FlagsResponse) -> Optional[dict[str, FlagValue]]:
         return None
 
     flags = response.get("flags", {})
-    return {key: value.get_value() for key, value in flags.items() if isinstance(value, FeatureFlag)}
+    return {
+        key: value.get_value()
+        for key, value in flags.items()
+        if isinstance(value, FeatureFlag)
+    }
 
 
 def to_payloads(response: FlagsResponse) -> Optional[dict[str, str]]:
@@ -262,5 +303,46 @@ def to_payloads(response: FlagsResponse) -> Optional[dict[str, str]]:
     return {
         key: value.metadata.payload
         for key, value in response.get("flags", {}).items()
-        if isinstance(value, FeatureFlag) and value.enabled and value.metadata.payload
+        if isinstance(value, FeatureFlag)
+        and value.enabled
+        and value.metadata.payload is not None
     }
+
+
+class FeatureFlagError:
+    """Error type constants for the $feature_flag_error property.
+
+    These values are sent in analytics events to track flag evaluation failures.
+    They should not be changed without considering impact on existing dashboards
+    and queries that filter on these values.
+
+    Error values:
+        ERRORS_WHILE_COMPUTING: Server returned errorsWhileComputingFlags=true
+        FLAG_MISSING: Requested flag not in API response
+        QUOTA_LIMITED: Rate/quota limit exceeded
+        TIMEOUT: Request timed out
+        CONNECTION_ERROR: Network connectivity issue
+        UNKNOWN_ERROR: Unexpected exceptions
+
+    For API errors with status codes, use the api_error() method which returns
+    a string like "api_error_500".
+    """
+
+    ERRORS_WHILE_COMPUTING = "errors_while_computing_flags"
+    FLAG_MISSING = "flag_missing"
+    QUOTA_LIMITED = "quota_limited"
+    TIMEOUT = "timeout"
+    CONNECTION_ERROR = "connection_error"
+    UNKNOWN_ERROR = "unknown_error"
+
+    @staticmethod
+    def api_error(status: Union[int, str]) -> str:
+        """Generate API error string with status code.
+
+        Args:
+            status: HTTP status code from the API error
+
+        Returns:
+            Error string like "api_error_500"
+        """
+        return f"api_error_{status}"

posthog/utils.py

@@ -1,11 +1,17 @@
+import json
 import logging
 import numbers
 import re
+import time
 from collections import defaultdict
 from dataclasses import asdict, is_dataclass
 from datetime import date, datetime, timezone
 from decimal import Decimal
+from typing import Any, Optional
 from uuid import UUID
+import sys
+import platform
+import distro  # For Linux OS detection
 
 import six
 from dateutil.tz import tzlocal, tzutc
@@ -52,7 +58,9 @@ def clean(item):
         return float(item)
     if isinstance(item, UUID):
         return str(item)
-    if isinstance(item, (six.string_types, bool, numbers.Number, datetime, date, type(None))):
+    if isinstance(
+        item, (six.string_types, bool, numbers.Number, datetime, date, type(None))
+    ):
         return item
     if isinstance(item, (set, list, tuple)):
         return _clean_list(item)
@@ -99,14 +107,35 @@ def _clean_dataclass(dataclass_):
     return data
 
 
-def _coerce_unicode(cmplx):
+def _coerce_unicode(cmplx: Any) -> Optional[str]:
+    """
+    In theory, this method is only called
+    after many isinstance checks are carried out in `utils.clean`.
+    When we supported Python 2 it was safe to call `decode` on a `str`
+    but in Python 3 that will throw.
+    So, we check if the input is bytes and only call `decode` in that case.
+
+    Previously we would always call `decode` on the input
+    That would throw an error.
+    Then we would call `decode` on the stringified error
+    That would throw an error.
+    And then we would return `None`
+
+    To avoid a breaking change, we can maintain the behavior
+    that anything which did not have `decode` in Python 2
+    returns None.
+    """
+    item = None
     try:
-        item = cmplx.decode("utf-8", "strict")
-    except AttributeError as exception:
-        item = ":".join(exception)
-        item.decode("utf-8", "strict")
+        if isinstance(cmplx, bytes):
+            item = cmplx.decode("utf-8", "strict")
+        elif isinstance(cmplx, str):
+            item = cmplx
+    except Exception as exception:
+        item = ":".join(map(str, exception.args))
         log.warning("Error decoding: %s", item)
         return None
+
     return item
 
 
@@ -130,6 +159,266 @@ class SizeLimitedDict(defaultdict):
         super().__setitem__(key, value)
 
 
+class FlagCacheEntry:
+    def __init__(self, flag_result, flag_definition_version, timestamp=None):
+        self.flag_result = flag_result
+        self.flag_definition_version = flag_definition_version
+        self.timestamp = timestamp or time.time()
+
+    def is_valid(self, current_time, ttl, current_flag_version):
+        time_valid = (current_time - self.timestamp) < ttl
+        version_valid = self.flag_definition_version == current_flag_version
+        return time_valid and version_valid
+
+    def is_stale_but_usable(self, current_time, max_stale_age=3600):
+        return (current_time - self.timestamp) < max_stale_age
+
+
+class FlagCache:
+    def __init__(self, max_size=10000, default_ttl=300):
+        self.cache = {}  # distinct_id -> {flag_key: FlagCacheEntry}
+        self.access_times = {}  # distinct_id -> last_access_time
+        self.max_size = max_size
+        self.default_ttl = default_ttl
+
+    def get_cached_flag(self, distinct_id, flag_key, current_flag_version):
+        current_time = time.time()
+
+        if distinct_id not in self.cache:
+            return None
+
+        user_flags = self.cache[distinct_id]
+        if flag_key not in user_flags:
+            return None
+
+        entry = user_flags[flag_key]
+        if entry.is_valid(current_time, self.default_ttl, current_flag_version):
+            self.access_times[distinct_id] = current_time
+            return entry.flag_result
+
+        return None
+
+    def get_stale_cached_flag(self, distinct_id, flag_key, max_stale_age=3600):
+        current_time = time.time()
+
+        if distinct_id not in self.cache:
+            return None
+
+        user_flags = self.cache[distinct_id]
+        if flag_key not in user_flags:
+            return None
+
+        entry = user_flags[flag_key]
+        if entry.is_stale_but_usable(current_time, max_stale_age):
+            return entry.flag_result
+
+        return None
+
+    def set_cached_flag(
+        self, distinct_id, flag_key, flag_result, flag_definition_version
+    ):
+        current_time = time.time()
+
+        # Evict LRU users if we're at capacity
+        if distinct_id not in self.cache and len(self.cache) >= self.max_size:
+            self._evict_lru()
+
+        # Initialize user cache if needed
+        if distinct_id not in self.cache:
+            self.cache[distinct_id] = {}
+
+        # Store the flag result
+        self.cache[distinct_id][flag_key] = FlagCacheEntry(
+            flag_result, flag_definition_version, current_time
+        )
+        self.access_times[distinct_id] = current_time
+
+    def invalidate_version(self, old_version):
+        users_to_remove = []
+
+        for distinct_id, user_flags in self.cache.items():
+            flags_to_remove = []
+            for flag_key, entry in user_flags.items():
+                if entry.flag_definition_version == old_version:
+                    flags_to_remove.append(flag_key)
+
+            # Remove invalidated flags
+            for flag_key in flags_to_remove:
+                del user_flags[flag_key]
+
+            # Remove user entirely if no flags remain
+            if not user_flags:
+                users_to_remove.append(distinct_id)
+
+        # Clean up empty users
+        for distinct_id in users_to_remove:
+            del self.cache[distinct_id]
+            if distinct_id in self.access_times:
+                del self.access_times[distinct_id]
+
+    def _evict_lru(self):
+        if not self.access_times:
+            return
+
+        # Remove 20% of least recently used entries
+        sorted_users = sorted(self.access_times.items(), key=lambda x: x[1])
+        to_remove = max(1, len(sorted_users) // 5)
+
+        for distinct_id, _ in sorted_users[:to_remove]:
+            if distinct_id in self.cache:
+                del self.cache[distinct_id]
+            if distinct_id in self.access_times:
+                del self.access_times[distinct_id]
+
+    def clear(self):
+        self.cache.clear()
+        self.access_times.clear()
+
+
+class RedisFlagCache:
+    def __init__(
+        self, redis_client, default_ttl=300, stale_ttl=3600, key_prefix="posthog:flags:"
+    ):
+        self.redis = redis_client
+        self.default_ttl = default_ttl
+        self.stale_ttl = stale_ttl
+        self.key_prefix = key_prefix
+        self.version_key = f"{key_prefix}version"
+
+    def _get_cache_key(self, distinct_id, flag_key):
+        return f"{self.key_prefix}{distinct_id}:{flag_key}"
+
+    def _serialize_entry(self, flag_result, flag_definition_version, timestamp=None):
+        if timestamp is None:
+            timestamp = time.time()
+
+        # Use clean to make flag_result JSON-serializable for cross-platform compatibility
+        serialized_result = clean(flag_result)
+
+        entry = {
+            "flag_result": serialized_result,
+            "flag_version": flag_definition_version,
+            "timestamp": timestamp,
+        }
+        return json.dumps(entry)
+
+    def _deserialize_entry(self, data):
+        try:
+            entry = json.loads(data)
+            flag_result = entry["flag_result"]
+            return FlagCacheEntry(
+                flag_result=flag_result,
+                flag_definition_version=entry["flag_version"],
+                timestamp=entry["timestamp"],
+            )
+        except (json.JSONDecodeError, KeyError, ValueError):
+            # If deserialization fails, treat as cache miss
+            return None
+
+    def get_cached_flag(self, distinct_id, flag_key, current_flag_version):
+        try:
+            cache_key = self._get_cache_key(distinct_id, flag_key)
+            data = self.redis.get(cache_key)
+
+            if data:
+                entry = self._deserialize_entry(data)
+                if entry and entry.is_valid(
+                    time.time(), self.default_ttl, current_flag_version
+                ):
+                    return entry.flag_result
+
+            return None
+        except Exception:
+            # Redis error - return None to fall back to normal evaluation
+            return None
+
+    def get_stale_cached_flag(self, distinct_id, flag_key, max_stale_age=None):
+        try:
+            if max_stale_age is None:
+                max_stale_age = self.stale_ttl
+
+            cache_key = self._get_cache_key(distinct_id, flag_key)
+            data = self.redis.get(cache_key)
+
+            if data:
+                entry = self._deserialize_entry(data)
+                if entry and entry.is_stale_but_usable(time.time(), max_stale_age):
+                    return entry.flag_result
+
+            return None
+        except Exception:
+            # Redis error - return None
+            return None
+
+    def set_cached_flag(
+        self, distinct_id, flag_key, flag_result, flag_definition_version
+    ):
+        try:
+            cache_key = self._get_cache_key(distinct_id, flag_key)
+            serialized_entry = self._serialize_entry(
+                flag_result, flag_definition_version
+            )
+
+            # Set with TTL for automatic cleanup (use stale_ttl for total lifetime)
+            self.redis.setex(cache_key, self.stale_ttl, serialized_entry)
+
+            # Update the current version
+            self.redis.set(self.version_key, flag_definition_version)
+
+        except Exception:
+            # Redis error - silently fail, don't break flag evaluation
+            pass
+
+    def invalidate_version(self, old_version):
+        try:
+            # For Redis, we use a simple approach: scan for keys with old version
+            # and delete them. This could be expensive with many keys, but it's
+            # necessary for correctness.
+
+            cursor = 0
+            pattern = f"{self.key_prefix}*"
+
+            while True:
+                cursor, keys = self.redis.scan(cursor, match=pattern, count=100)
+
+                for key in keys:
+                    if key.decode() == self.version_key:
+                        continue
+
+                    try:
+                        data = self.redis.get(key)
+                        if data:
+                            entry_dict = json.loads(data)
+                            if entry_dict.get("flag_version") == old_version:
+                                self.redis.delete(key)
+                    except (json.JSONDecodeError, KeyError):
+                        # If we can't parse the entry, delete it to be safe
+                        self.redis.delete(key)
+
+                if cursor == 0:
+                    break
+
+        except Exception:
+            # Redis error - silently fail
+            pass
+
+    def clear(self):
+        try:
+            # Delete all keys matching our pattern
+            cursor = 0
+            pattern = f"{self.key_prefix}*"
+
+            while True:
+                cursor, keys = self.redis.scan(cursor, match=pattern, count=100)
+                if keys:
+                    self.redis.delete(*keys)
+                if cursor == 0:
+                    break
+        except Exception:
+            # Redis error - silently fail
+            pass
+
+
 def convert_to_datetime_aware(date_obj):
     if date_obj.tzinfo is None:
         date_obj = date_obj.replace(tzinfo=timezone.utc)
@@ -174,3 +463,57 @@ def str_iequals(value, comparand):
         False
     """
     return str(value).casefold() == str(comparand).casefold()
+
+
+def get_os_info():
+    """
+    Returns standardized OS name and version information.
+    Similar to how user agent parsing works in JS.
+    """
+    os_name = ""
+    os_version = ""
+
+    platform_name = sys.platform
+
+    if platform_name.startswith("win"):
+        os_name = "Windows"
+        if hasattr(platform, "win32_ver"):
+            win_version = platform.win32_ver()[0]
+            if win_version:
+                os_version = win_version
+
+    elif platform_name == "darwin":
+        os_name = "Mac OS X"
+        if hasattr(platform, "mac_ver"):
+            mac_version = platform.mac_ver()[0]
+            if mac_version:
+                os_version = mac_version
+
+    elif platform_name.startswith("linux"):
+        os_name = "Linux"
+        linux_info = distro.info()
+        if linux_info["version"]:
+            os_version = linux_info["version"]
+
+    elif platform_name.startswith("freebsd"):
+        os_name = "FreeBSD"
+        if hasattr(platform, "release"):
+            os_version = platform.release()
+
+    else:
+        os_name = platform_name
+        if hasattr(platform, "release"):
+            os_version = platform.release()
+
+    return os_name, os_version
+
+
+def system_context() -> dict[str, Any]:
+    os_name, os_version = get_os_info()
+
+    return {
+        "$python_runtime": platform.python_implementation(),
+        "$python_version": "%s.%s.%s" % (sys.version_info[:3]),
+        "$os": os_name,
+        "$os_version": os_version,
+    }

posthog/version.py

@@ -1,4 +1,4 @@
-VERSION = "4.0.0"
+VERSION = "7.6.0"
 
 if __name__ == "__main__":
     print(VERSION, end="")  # noqa: T201

pyproject.toml

@@ -1,10 +1,100 @@
-[tool.black]
-line-length = 120
+[build-system]
+requires = ["setuptools>=61.0", "wheel"]
+build-backend = "setuptools.build_meta"
 
-[tool.isort]
-multi_line_output = 3
-include_trailing_comma = true
-force_grid_wrap = 8
-ensure_newline_before_comments = true
-line_length = 120
-virtual_env = "env"
+[project]
+name = "posthog"
+dynamic = ["version"]
+description = "Integrate PostHog into any python application."
+authors = [{ name = "PostHog", email = "hey@posthog.com" }]
+maintainers = [{ name = "PostHog", email = "hey@posthog.com" }]
+license = { text = "MIT" }
+readme = "README.md"
+requires-python = ">=3.10"
+classifiers = [
+    "Development Status :: 5 - Production/Stable",
+    "Intended Audience :: Developers",
+    "Operating System :: OS Independent",
+    "License :: OSI Approved :: MIT License",
+    "Programming Language :: Python",
+    "Programming Language :: Python :: 3.10",
+    "Programming Language :: Python :: 3.11",
+    "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
+    "Programming Language :: Python :: 3.14",
+]
+dependencies = [
+    "requests>=2.7,<3.0",
+    "six>=1.5",
+    "python-dateutil>=2.2",
+    "backoff>=1.10.0",
+    "distro>=1.5.0",
+    "typing-extensions>=4.2.0",
+]
+
+[project.urls]
+Homepage = "https://github.com/posthog/posthog-python"
+Repository = "https://github.com/posthog/posthog-python"
+
+[project.optional-dependencies]
+langchain = ["langchain>=0.2.0"]
+dev = [
+    "django-stubs",
+    "lxml",
+    "mypy",
+    "mypy-baseline",
+    "types-mock",
+    "types-python-dateutil",
+    "types-requests",
+    "types-setuptools",
+    "types-six",
+    "pre-commit",
+    "pydantic",
+    "ruff",
+    "setuptools",
+    "packaging",
+    "wheel",
+    "twine",
+    "tomli",
+    "tomli_w",
+]
+test = [
+    "mock>=2.0.0",
+    "freezegun==1.5.1",
+    "coverage",
+    "pytest",
+    "pytest-timeout",
+    "pytest-asyncio",
+    "django",
+    "openai>=2.0",
+    "anthropic>=0.72",
+    "langgraph>=1.0",
+    "langchain-core>=1.0",
+    "langchain-community>=0.4",
+    "langchain-openai>=1.0",
+    "langchain-anthropic>=1.0",
+    "google-genai",
+    "pydantic",
+    "parameterized>=0.8.1",
+]
+
+[tool.setuptools]
+packages = [
+    "posthog",
+    "posthog.ai",
+    "posthog.ai.langchain",
+    "posthog.ai.openai",
+    "posthog.ai.anthropic",
+    "posthog.ai.gemini",
+    "posthog.test",
+    "posthog.integrations",
+]
+
+[tool.setuptools.dynamic]
+version = { attr = "posthog.version.VERSION" }
+
+[tool.pytest.ini_options]
+asyncio_mode = "auto"
+asyncio_default_fixture_loop_scope = "function"
+testpaths = ["posthog/test"]
+norecursedirs = ["integration_tests"]