YoannAbriel opened a new pull request, #62883:
URL: https://github.com/apache/airflow/pull/62883

   ## Problem
   
   When using `KeycloakAuthManager` (or any auth manager) with symmetric JWT 
signing (HS256 + secret key), the authentication flow enters an infinite 
redirect loop. After successful login, the internal session JWT is rejected by 
the FastAPI `JWTValidator` with: `Missing 'kid' in token header`.
   
   ## Root Cause
   
   `JWTGenerator.generate()` only added the `kid` field to the JWT header when 
using asymmetric (private key) signing. Symmetric (secret key) tokens never got 
`kid` in the header. However, `JWTValidator._get_kid_from_header()` 
unconditionally requires `kid` in the token header, causing all symmetric-key 
tokens to fail validation.
   
   Additionally, `_generate_kid()` returned `"not-used"` immediately for 
symmetric keys without checking the `api_auth.jwt_kid` configuration, so 
operators couldn't set a meaningful `kid` for their symmetric setup.
   
   ## Fix
   
   Two changes in `airflow-core/src/airflow/api_fastapi/auth/tokens.py`:
   
   1. **Always include `kid` in the JWT header** — removed the `if 
self._private_key:` guard so `headers["kid"] = self.kid` runs for both 
symmetric and asymmetric keys.
   2. **Check configured `jwt_kid` before falling back** — reordered 
`_generate_kid()` to check the `api_auth.jwt_kid` config option first, before 
returning the `"not-used"` fallback for symmetric keys. This lets operators 
configure a custom `kid` regardless of key type.
   
   Added two unit tests: one verifying symmetric tokens include `kid` in the 
header, another verifying the configured `jwt_kid` is respected for symmetric 
keys.
   
   Closes: #62876
   
   <!-- SPDX-License-Identifier: Apache-2.0
         https://www.apache.org/licenses/LICENSE-2.0 -->
   
   ---
   
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