# api key authentication context extraction fix

## problem identified

the `check_user_permissions` tool was returning "no email provided and no authenticated user found" when using api key authentication over sse, even though the user was successfully authenticated via the `apikeyTokenVerifier`.

## root cause analysis

the issue was in the `_get_authenticated_user_email` function in `src/tools/mcp_tools.py`. this function was looking for authenticated user information in the wrong places:

1. **api key authentication flow**: user authenticates via `apikeyTokenVerifier` which creates an `AccessToken` with user email in the `subject` field
2. **context extraction failure**: the function was only checking oauth-style authentication paths and not properly accessing the api key authentication context

## solution implemented

### 1. enhanced user email extraction

- completely rewrote `_get_authenticated_user_email` function to support multiple authentication methods
- added support for api key authentication via `session.access_token.subject`
- maintained backward compatibility with oauth authentication
- added comprehensive error handling and debug logging

### 2. improved authentication status reporting

- updated `check_user_permissions` to properly identify authentication method (api key vs oauth)
- enhanced status messages to show "✅ authenticated via api_key" instead of generic messages

### 3. added debug tooling

- created `debug_auth_context` tool to help troubleshoot authentication issues
- added debug mode to `_get_authenticated_user_email` function
- enabled debug logging in permissions check to help diagnose context structure

## key changes made

```python
def _get_authenticated_user_email(ctx, debug=False):
    # method 1: oauth authentication
    if hasattr(ctx, 'session') and hasattr(ctx.session, 'auth_context'):
        # ... oauth logic

    # method 2: api key authentication (new!)
    if hasattr(ctx, 'session') and hasattr(ctx.session, 'access_token'):
        if hasattr(ctx.session.access_token, 'subject'):
            return ctx.session.access_token.subject

    # method 3: alternative access patterns
    # ... additional fallback methods
```

### authentication method detection

```python
# determine auth method from context
if hasattr(access_token, 'extra') and access_token.extra:
    auth_method = access_token.extra.get('auth_method', 'token-based')
```

## testing approach

1. **debug tool**: run `debug_auth_context` to understand context structure
2. **permissions check**: run `check_user_permissions` without email to test authenticated user extraction
3. **verify auth method**: ensure status shows "✅ authenticated via api_key"

## expected outcome

- `check_user_permissions` tool should now work with api key authentication
- should display proper authentication status and user permissions
- no email parameter required when user is authenticated via api key

## files modified

- `src/tools/mcp_tools.py`: main authentication context extraction logic
- added comprehensive debug logging and new debug tool

## follow-up fix: pydantic validation error

after initial implementation, encountered pydantic validation error:
```
1 validation error for check_user_permissionsArguments
email
  Input should be a valid string [type=string_type, input_value=None, input_type=NoneType]
```

**root cause**: type annotation was `email: str = None` but should allow none values

**fix applied**: changed type annotation to `email: Optional[str] = None`

```python
# before (broken)
def check_user_permissions(email: str = None, ctx = None):

# after (fixed)  
def check_user_permissions(email: Optional[str] = None, ctx = None):
```

## next steps

1. test with running sse server and api key authentication
2. verify all tools work properly with authenticated users  
3. remove debug logging once confirmed working
4. consider adding similar fixes to other servers if needed

## status: ✅ ready for testing

both the authentication context extraction and pydantic validation issues have been resolved.

