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.agent-os/product/roadmap.md

@@ -26,17 +26,17 @@ The following features have been implemented:
 
 ### Must-Have Features (Current MVP Focus)
 
-- [ ] **Complete Booking System** - Full calendar booking with partner availability `L` 🔄
-- [ ] **Payment Authorization Flow** - $800 session pre-authorization before meetings `M` 🔄
-- [ ] **Google Meet Integration** - Automatic meeting link generation and calendar invites `M`
-- [ ] **Confirmation Email System** - Automated emails for booking confirmations `S`
-- [ ] **Session Management** - Partners can start meetings and access client info `M`
+- [x] **Complete Booking System** - Full calendar booking with partner availability `L` 🔄
+- [x] **Payment Authorization Flow** - $800 session pre-authorization before meetings `M` 🔄
+- [x] **Google Meet Integration** - Automatic meeting link generation and calendar invites `M`
+- [x] **Confirmation Email System** - Automated emails for booking confirmations `S`
+- [x] **Session Management** - Partners can start meetings and access client info `M`
 
 ### Should-Have Features
 
-- [ ] **Partner Availability Management** - Real-time availability calendar updates `M`
-- [ ] **Basic Note-Taking** - Partner session notes with client association `S`
-- [ ] **Payment Capture** - Complete payment after successful session `S`
+- [x] **Partner Availability Management** - Real-time availability calendar updates `M`
+- [x] **Basic Note-Taking** - Partner session notes with client association `S`
+- [x] **Payment Capture** - Complete payment after successful session `S`
 
 ### Dependencies
 
@@ -150,4 +150,4 @@ The following features have been implemented:
 - **S:** 2-3 days  
 - **M:** 1 week
 - **L:** 2 weeks
-- **XL:** 3+ weeks
+- **XL:** 3+ weeks

.agent-os/specs/2025-08-07-e2e-google-oauth-auth/spec.md

@@ -0,0 +1,62 @@
+# Spec Requirements Document
+
+> Spec: E2E Google OAuth Authentication Handler  
+> Created: 2025-08-07  
+> Status: Planning
+
+## Overview
+
+Implement automated Google OAuth authentication handling in Playwright E2E tests to enable comprehensive testing of user workflows that require authentication. This feature will allow tests to automatically authenticate users via Google and wait for authentication completion, enabling full end-to-end testing of the consultation booking platform.
+
+## User Stories
+
+### Test Automation Story
+
+As an **E2E Test Engineer**, I want to automatically handle Google OAuth authentication during test execution, so that I can test the complete user journey from authentication through booking without manual intervention.
+
+**Detailed Workflow:**
+1. Test navigates to application and encounters Keycloak login page
+2. Test clicks "Sign in with Google" button
+3. Test handles OAuth redirect to Google authentication
+4. Test automatically provides test credentials or waits for manual authentication
+5. Test waits for OAuth callback and authentication completion
+6. Test continues with authenticated user session to test booking workflow
+
+### Quality Assurance Story
+
+As a **QA Engineer**, I want E2E tests that validate the complete authenticated user experience, so that I can ensure the booking workflow works correctly for real users who authenticate via Google.
+
+**Detailed Workflow:**
+1. QA runs comprehensive test suite including authentication scenarios
+2. Tests handle authentication automatically or with minimal manual intervention
+3. Tests validate post-authentication state and user session
+4. Tests execute complete booking workflow with authenticated context
+5. Tests verify authentication persistence across page navigation
+
+## Spec Scope
+
+1. **Google OAuth Flow Integration** - Implement Playwright handlers for Google OAuth redirect and callback flows
+2. **Authentication State Management** - Detect and wait for authentication completion with session validation
+3. **Test Credential Management** - Secure handling of test Google account credentials for automated authentication
+4. **Session Persistence Testing** - Validate authentication session maintains across page navigation and interactions
+5. **Authentication Timeout Handling** - Implement robust timeout and retry mechanisms for authentication flows
+
+## Out of Scope
+
+- Modifying the application's authentication implementation (Keycloak configuration)
+- Testing other OAuth providers (Facebook, Microsoft, etc.) - Google only
+- Implementing new authentication flows in the application
+- User account management or test data provisioning beyond authentication
+- Performance testing of authentication flows
+
+## Expected Deliverable
+
+1. **Automated E2E Tests** - P0 tests (CompleteBookingWorkflow, PaymentAuthorization, AIPartnerMatching) successfully execute with Google OAuth authentication
+2. **Authentication Helper Methods** - Reusable Page Object Model methods for handling Google OAuth in any test scenario
+3. **Test Configuration** - Environment-based configuration for test Google account credentials and authentication timeouts
+
+## Spec Documentation
+
+- Tasks: @.agent-os/specs/2025-08-07-e2e-google-oauth-auth/tasks.md
+- Technical Specification: @.agent-os/specs/2025-08-07-e2e-google-oauth-auth/sub-specs/technical-spec.md
+- Tests Specification: @.agent-os/specs/2025-08-07-e2e-google-oauth-auth/sub-specs/tests.md

.agent-os/specs/2025-08-07-e2e-google-oauth-auth/sub-specs/technical-spec.md

@@ -0,0 +1,117 @@
+# Technical Specification
+
+This is the technical specification for the spec detailed in @.agent-os/specs/2025-08-07-e2e-google-oauth-auth/spec.md
+
+> Created: 2025-08-07  
+> Version: 1.0.0
+
+## Technical Requirements
+
+### Authentication Flow Requirements
+- **OAuth Redirect Handling**: Playwright must follow OAuth redirects from Keycloak to Google and back
+- **Dynamic URL Detection**: Handle Google OAuth URLs that change dynamically during authentication flow
+- **Session State Validation**: Verify authentication completion by detecting authenticated page elements or user context
+- **Cross-Domain Cookie Handling**: Ensure OAuth cookies are properly managed across domains during flow
+- **Error State Detection**: Identify and handle authentication failures, timeouts, or user cancellations
+
+### Test Environment Requirements
+- **Test Account Management**: Secure storage and retrieval of Google test account credentials
+- **Environment Configuration**: Support for different authentication modes (automated vs manual) per environment
+- **Browser Context Isolation**: Ensure authentication state doesn't leak between test runs
+- **Headless vs Headed Mode**: Support both modes with appropriate authentication handling strategies
+
+### Performance and Reliability Requirements
+- **Authentication Timeout**: 60-second timeout for complete OAuth flow completion
+- **Retry Mechanisms**: Automatic retry for transient authentication failures (network, OAuth provider issues)
+- **State Synchronization**: Robust waiting mechanisms for OAuth callback processing
+- **Evidence Collection**: Screenshots and logs captured during authentication flow for debugging
+
+## Approach Options
+
+**Option A: Automated Test Credentials** 
+- Pros: Fully automated testing, consistent results, no manual intervention required
+- Cons: Security concerns with storing credentials, potential account lockout risks, brittle to Google security changes
+
+**Option B: Manual Authentication with Test Waiting** (Selected)
+- Pros: More secure (no stored credentials), flexible for different test scenarios, works with any Google account
+- Cons: Requires manual intervention during test runs, slower execution, not suitable for CI/CD
+
+**Option C: OAuth Token Mocking**
+- Pros: No real OAuth dependency, fast execution, no credential management
+- Cons: Doesn't test real authentication integration, may miss OAuth-related bugs, complex setup
+
+**Rationale:** Option B provides the best balance of security, reliability, and comprehensive testing. It allows real OAuth flow testing without credential security risks, making it suitable for the current testing needs while maintaining flexibility for future automation.
+
+## Implementation Architecture
+
+### Page Object Model Integration
+```csharp
+public class AuthenticationPage : BasePage
+{
+    public async Task<bool> HandleGoogleOAuthAsync(int timeoutMs = 60000)
+    public async Task WaitForAuthenticationCompletionAsync()
+    public async Task<bool> IsUserAuthenticatedAsync()
+}
+```
+
+### Test Configuration Structure
+```json
+{
+  "Authentication": {
+    "Mode": "Manual", // "Automated" | "Manual"  
+    "Timeout": 60000,
+    "RetryAttempts": 3,
+    "TestAccount": {
+      "Email": "test@example.com", // Only if Mode = "Automated"
+      "Password": "***" // Only if Mode = "Automated"
+    }
+  }
+}
+```
+
+### Authentication Flow Implementation
+1. **Detect Authentication Redirect**: Monitor page navigation for Keycloak → Google OAuth URLs
+2. **Handle OAuth Flow**: Wait for user to complete Google authentication manually
+3. **Monitor Callback**: Detect OAuth callback URL and wait for application to process authentication
+4. **Validate Session**: Verify authenticated state by checking for user-specific UI elements
+5. **Continue Test**: Proceed with authenticated test scenario execution
+
+## External Dependencies
+
+- **Microsoft.Playwright.NUnit** (existing) - Core testing framework
+- **Microsoft.Extensions.Configuration** (existing) - Configuration management for test settings
+- **System.Text.Json** (existing) - JSON configuration parsing
+
+**No New Dependencies Required** - Implementation uses existing Playwright capabilities and .NET standard libraries.
+
+## Security Considerations
+
+### Test Account Security
+- Test credentials (if used) stored in secure configuration (User Secrets, environment variables)
+- No credentials committed to version control
+- Separate test Google account isolated from production systems
+- Regular credential rotation recommended
+
+### OAuth Flow Security
+- Tests operate in isolated browser contexts to prevent session leakage
+- Authentication tokens not persisted beyond test execution
+- OAuth redirects validated to prevent redirect attacks during testing
+
+### Environment Isolation
+- Test authentication flows use dedicated test Google account
+- Test runs in isolated browser profiles to prevent cross-contamination
+- Authentication state cleared between test runs
+
+## Error Handling Strategy
+
+### Authentication Failure Scenarios
+- **OAuth Provider Unavailable**: Retry with exponential backoff, fail gracefully with clear error message
+- **User Cancellation**: Detect cancellation and skip authentication-dependent tests
+- **Timeout During Flow**: Clear error message indicating manual intervention timeout
+- **Invalid Credentials**: Clear failure indication for automated credential scenarios
+
+### Recovery Mechanisms
+- Automatic browser context reset on authentication failure
+- Test suite continues with non-authenticated scenarios if possible
+- Detailed logging and screenshots for authentication failure debugging
+- Graceful degradation to manual authentication prompts when automated fails

.agent-os/specs/2025-08-07-e2e-google-oauth-auth/sub-specs/tests.md

@@ -0,0 +1,126 @@
+# Tests Specification
+
+This is the tests coverage details for the spec detailed in @.agent-os/specs/2025-08-07-e2e-google-oauth-auth/spec.md
+
+> Created: 2025-08-07  
+> Version: 1.0.0
+
+## Test Coverage
+
+### Unit Tests
+
+**AuthenticationPage (Page Object Model)**
+- HandleGoogleOAuthAsync returns true when authentication completes successfully
+- HandleGoogleOAuthAsync returns false when authentication times out
+- WaitForAuthenticationCompletionAsync detects authenticated state correctly
+- IsUserAuthenticatedAsync correctly identifies authenticated vs unauthenticated states
+- OAuth redirect detection works with various Google OAuth URL patterns
+- Browser context isolation prevents session leakage between tests
+
+**Configuration Management**
+- Authentication configuration loads correctly from test settings
+- Missing configuration values handled with appropriate defaults
+- Invalid configuration values rejected with clear error messages
+- Credential loading from secure storage (User Secrets) works correctly
+
+### Integration Tests
+
+**Complete OAuth Flow Integration**
+- End-to-end OAuth flow from Keycloak → Google → Application callback → Authenticated state
+- OAuth flow works correctly in both headless and headed browser modes
+- Authentication state persists correctly across page navigation within test
+- Multiple authentication attempts handle session cleanup correctly
+- Browser context reset clears authentication state between test runs
+
+**Error Scenarios Integration**  
+- Authentication timeout handled gracefully without hanging test execution
+- Invalid OAuth callback URLs detected and handled appropriately
+- Network failures during OAuth flow trigger appropriate retry mechanisms
+- Authentication cancellation by user handled without test failure
+
+### Feature Tests (E2E Scenarios)
+
+**Authenticated User Journey**
+- Complete booking workflow executes successfully after Google OAuth authentication
+- Payment authorization flow works correctly with authenticated user context
+- AI partner matching functions properly with authenticated user session
+- Partner profile viewing and selection works with authenticated context
+- Session persistence maintained throughout entire booking workflow
+
+**Authentication State Validation**
+- Authenticated user sees personalized content and user-specific navigation
+- Authentication state correctly reflected in UI elements and user context
+- Logout functionality works correctly and clears authentication state
+- Re-authentication after session expiry handles correctly
+
+**Cross-Browser Authentication Testing**
+- Google OAuth flow works correctly across Chromium, Firefox, and WebKit browsers
+- Authentication state handling consistent across different browser implementations
+- OAuth cookies and session management work correctly in all browsers
+
+### Mocking Requirements
+
+**OAuth Provider Mocking (For Offline Testing)**
+- **Google OAuth Endpoints:** Mock OAuth authorization and token endpoints for offline test execution
+- **Keycloak Integration:** Mock Keycloak OAuth configuration for testing authentication flow setup
+- **Network Conditions:** Simulate network failures, slow responses, and intermittent connectivity during OAuth flow
+
+**Authentication State Mocking**
+- **Session Cookies:** Mock authenticated session cookies for testing post-authentication scenarios
+- **User Context:** Mock authenticated user data and permissions for testing user-specific functionality
+- **OAuth Tokens:** Mock JWT tokens and refresh tokens for testing token-based authentication scenarios
+
+### Test Configuration Requirements
+
+**Environment-Specific Testing**
+- **Development Environment:** Manual authentication with extended timeouts for debugging
+- **CI/CD Environment:** Automated authentication with test credentials (if implemented)
+- **Local Testing:** Flexible authentication mode selection for developer convenience
+
+**Test Data Management**
+- **Test Accounts:** Isolated Google test account for authentication testing
+- **Session Management:** Proper cleanup of authentication state between test runs
+- **Parallel Execution:** Authentication tests can run in parallel without interference
+
+## Testing Strategy
+
+### Authentication Flow Testing
+1. **Pre-Authentication State**: Verify application correctly redirects to authentication
+2. **OAuth Initiation**: Verify OAuth flow begins correctly with proper parameters
+3. **Google Authentication**: Handle or verify Google authentication page interaction
+4. **OAuth Callback**: Verify callback processing and token exchange
+5. **Post-Authentication State**: Verify authenticated user context and UI updates
+6. **Session Persistence**: Verify authentication maintained across application navigation
+
+### Error Handling Testing
+1. **Timeout Scenarios**: Verify graceful handling of authentication timeouts
+2. **Network Failures**: Test retry mechanisms for network issues during OAuth flow
+3. **Invalid Responses**: Verify handling of malformed OAuth responses
+4. **User Cancellation**: Test behavior when user cancels authentication
+5. **Provider Unavailable**: Test fallback behavior when Google OAuth is unavailable
+
+### Performance Testing
+1. **Authentication Timing**: Verify OAuth flow completes within acceptable time limits
+2. **Session Loading**: Verify authenticated session loads quickly after OAuth completion
+3. **Concurrent Authentication**: Test multiple authentication flows don't interfere
+4. **Resource Cleanup**: Verify proper cleanup of authentication resources after tests
+
+## Test Execution Guidelines
+
+### Local Development Testing
+- Use headed browser mode for authentication debugging and manual intervention
+- Extended timeouts (120 seconds) for manual authentication completion
+- Detailed logging enabled for authentication flow troubleshooting
+- Screenshots captured at each authentication step for visual verification
+
+### Continuous Integration Testing
+- Headless browser mode with automated authentication (if credentials available)
+- Standard timeouts (60 seconds) for automated flow completion
+- Error handling and retry mechanisms enabled
+- Test failure artifacts (logs, screenshots) preserved for debugging
+
+### Test Result Validation
+- Authentication success/failure clearly reported in test results
+- Authentication timing metrics captured for performance monitoring
+- Authentication errors categorized (timeout, network, provider, user) for analysis
+- Post-authentication test coverage metrics tracked for completeness validation