OCR/openspec/changes/migrate-to-external-api-authentication/tasks.md

Implementation Tasks

1. Database Schema Updates

• 1.1 Create database migration script
  • Add external_user_id column (VARCHAR 255)
  • Add display_name column (VARCHAR 255)
  • Add azure_email column (VARCHAR 255)
  • Add last_token_refresh column (DATETIME)
  • Mark hashed_password as nullable (for gradual migration)
• 1.2 Update User model
  • Add new fields to SQLAlchemy model
  • Update model relationships if needed
  • Add migration version with Alembic
• 1.3 Create user sync mechanism
  • Script to map existing users to external IDs
  • Handle users without external accounts
  • Backup existing user data

2. Configuration Management

• 2.1 Update environment configuration
  • Add EXTERNAL_AUTH_API_URL to .env.local
  • Add EXTERNAL_AUTH_ENDPOINT configuration
  • Add EXTERNAL_AUTH_TIMEOUT setting
  • Add USE_EXTERNAL_AUTH feature flag
  • Add TOKEN_REFRESH_BUFFER setting
• 2.2 Update Settings class
  • Add external auth settings to backend/app/core/config.py
  • Add validation for new configuration values
  • Implement feature flag logic

3. External API Integration Service

• 3.1 Create auth API client
  • Implement backend/app/services/external_auth_service.py
  • Create async HTTP client for API calls
  • Implement request/response models
  • Add proper error handling and logging
• 3.2 Implement authentication methods
  • authenticate_user() - Call external API
  • validate_token() - Verify token validity
  • refresh_token() - Handle token refresh
  • get_user_info() - Fetch user details
• 3.3 Add resilience patterns
  • Implement retry logic with exponential backoff
  • Add circuit breaker pattern
  • Implement timeout handling
  • Add fallback mechanisms

4. Backend Authentication Updates

• 4.1 Modify login endpoint
  • Update backend/app/api/v1/endpoints/auth.py
  • Route to external API based on feature flag
  • Handle both authentication modes during transition
  • Return appropriate token format
• 4.2 Update token validation
  • Modify backend/app/core/security.py
  • Support both local and external tokens
  • Implement token type detection
  • Update JWT validation logic
• 4.3 Update authentication dependencies
  • Modify backend/app/core/auth.py
  • Update get_current_user() dependency
  • Handle external user information
  • Implement proper user context

5. Session and Token Management

• 5.1 Implement token storage
  • Store external tokens securely
  • Implement token encryption at rest
  • Handle multiple token types (access, ID, refresh)
• 5.2 Create token refresh mechanism
  • Background task for token refresh
  • Refresh tokens before expiration
  • Update stored tokens atomically
  • Handle refresh failures gracefully
• 5.3 Session invalidation
  • Clear tokens on logout
  • Handle token revocation
  • Implement session timeout

6. Frontend Updates

• 6.1 Update authentication service
  • Modify frontend/src/services/authService.ts
  • Handle new token format
  • Store user display information
  • Implement token refresh on client side
• 6.2 Update auth store
  • Modify frontend/src/stores/authStore.ts
  • Store external user information
  • Update user display logic
  • Handle token expiration
• 6.3 Update UI components
  • Modify frontend/src/components/Header.tsx
  • Display user name instead of username
  • Show additional user information
  • Update login form if needed
• 6.4 Error handling
  • Handle external API errors
  • Display appropriate error messages
  • Implement retry UI for failures
  • Add loading states

7. Testing

• 7.1 Unit tests
  • Test external auth service
  • Test token validation
  • Test user information mapping
  • Test error scenarios
• 7.2 Integration tests
  • Test full authentication flow
  • Test token refresh mechanism
  • Test fallback scenarios
  • Test feature flag switching
• 7.3 Load testing
  • Test external API response times
  • Test system under high authentication load
  • Measure impact on performance
• 7.4 Security testing
  • Test token security
  • Verify HTTPS enforcement
  • Test rate limiting
  • Validate error message security

8. Migration Execution

• 8.1 Pre-migration preparation
  • Backup database
  • Document rollback procedure
  • Prepare user communication
  • Set up monitoring
• 8.2 Staged rollout
  • Enable for test users first
  • Monitor for issues
  • Gradually increase user percentage
  • Collect feedback
• 8.3 Post-migration validation
  • Verify all users can login
  • Check audit logs
  • Monitor error rates
  • Validate performance metrics

9. Documentation

• 9.1 Technical documentation
  • Update API documentation
  • Document authentication flow
  • Update deployment guide
  • Create troubleshooting guide
• 9.2 User documentation
  • Update login instructions
  • Document new features
  • Create FAQ for common issues
• 9.3 Operations documentation
  • Document monitoring points
  • Create runbook for issues
  • Document rollback procedure

10. Monitoring and Observability

• 10.1 Add monitoring metrics
  • Authentication success/failure rates
  • External API response times
  • Token refresh success rate
  • Error rate monitoring
• 10.2 Implement logging
  • Log all authentication attempts
  • Log external API calls
  • Log token operations
  • Structured logging for analysis
• 10.3 Create alerts
  • Alert on high failure rates
  • Alert on external API unavailability
  • Alert on token refresh failures
  • Alert on unusual patterns

11. Cleanup (Post-Stabilization)

• 11.1 Remove legacy code
  • Remove local authentication code (after stable period)
  • Remove unused database columns
  • Clean up configuration
• 11.2 Optimize performance
  • Implement caching where appropriate
  • Optimize database queries
  • Review and optimize API calls