raphaelauv opened a new issue, #71664:
URL: https://github.com/apache/airflow/issues/71664

   ### Under which category would you file this issue?
   
   Airflow Core
   
   ### Apache Airflow version
   
   3.2.1
   
   ### What happened and how to reproduce it?
   
   when using a custom `airflowLocalSettings` ( airflow_local_settings.py )  in 
the helm chart
   
   ```yaml
   AIRFLOW__DATABASE__SQL_ALCHEMY_CONN : 
postgresql://airflow_iam_user:@XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX.rds.amazonaws.com:5432/airflow_db?sslmode=require
   ```
   
   ```yaml
   airflowLocalSettings: |-
     from sqlalchemy import create_engine, event
     import boto3
   
   
     def generate_rds_token(host, port, user, region):
         client = boto3.client('rds', region_name=region)
         return client.generate_db_auth_token(
             DBHostname=host,
             Port=port,
             DBUsername=user,
             Region=region
         )
   
   
     def create_metadata_engine(sql_alchemy_conn, *, engine_args, connect_args):
         connect_args["sslmode"]="require"
         engine = create_engine(
             sql_alchemy_conn,
             connect_args=connect_args,
             **engine_args,
             future=True,
         )
   
         @event.listens_for(engine, "do_connect")
         def provide_token(dialect, conn_rec, cargs, cparams):
             print("SYNC TOKEN RDS")
             token = generate_rds_token(
                 user=cparams["user"],
                 host=cparams["host"],
                 port=cparams["port"],
                 region=cparams["host"].split(".")[2])
             cparams["password"] = token
   
         return engine
   
   ```
   
   
   the `apiServer` fail to start but the `migrateDatabaseJob` run successfully
   
   ````log
     ____________       _____________
    ____    |__( )_________  __/__  /________      __
   ____  /| |_  /__  ___/_  /_ __  /_  __ \_ | /| / /
   ___  ___ |  / _  /   _  __/ _  / / /_/ /_ |/ |/ /
    _/_/  |_/_/  /_/    /_/    /_/  \____/____/|__/
   Running the API server with uvicorn:
   Apps: all
   Workers: 1
   Host: 0.0.0.0:8080
   Timeout: 120
   Logfiles: -
   =================================================================
   2026-08-15T23:04:01.809867Z [warning  ] starlette.middleware.wsgi is 
deprecated and will be removed in a future release. Please refer to 
https://github.com/abersheeran/a2wsgi as a replacement. [py.warnings] 
category=StarletteDeprecationWarning 
filename=/home/airflow/.local/lib/python3.14/site-packages/fastapi/middleware/wsgi.py
 lineno=1
   2026-08-15T23:04:03.050834Z [warning  ] 'return' in a 'finally' block  
[py.warnings] category=SyntaxWarning 
filename=/home/airflow/.local/lib/python3.14/site-packages/flask_appbuilder/baseviews.py
 lineno=1258
   2026-08-15T23:04:03.051039Z [warning  ] 'return' in a 'finally' block  
[py.warnings] category=SyntaxWarning 
filename=/home/airflow/.local/lib/python3.14/site-packages/flask_appbuilder/baseviews.py
 lineno=1305
   2026-08-15T23:04:04.005226Z [warning  ] Using the in-memory storage for 
tracking rate limits as no storage was explicitly specified. This is not 
recommended for production use. See: 
https://flask-limiter.readthedocs.io#configuring-a-storage-backend for 
documentation about configuring the storage backend. [py.warnings] 
category=UserWarning 
filename=/home/airflow/.local/lib/python3.14/site-packages/flask_limiter/_extension.py
 lineno=364
   Traceback (most recent call last):
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 144, in __init__
       self._dbapi_connection = engine.raw_connection()
                                ~~~~~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 3319, in raw_connection
       return self.pool.connect()
              ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 448, in connect
       return _ConnectionFairy._checkout(self)
              ~~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 1272, in _checkout
       fairy = _ConnectionRecord.checkout(pool)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 712, in checkout
       rec = pool._do_get()
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/impl.py", 
line 178, in _do_get
       with util.safe_reraise():
            ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/util/langhelpers.py",
 line 122, in __exit__
       raise exc_value.with_traceback(exc_tb)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/impl.py", 
line 176, in _do_get
       return self._create_connection()
              ~~~~~~~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 389, in _create_connection
       return _ConnectionRecord(self)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 674, in __init__
       self.__connect()
       ~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 900, in __connect
       with util.safe_reraise():
            ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/util/langhelpers.py",
 line 122, in __exit__
       raise exc_value.with_traceback(exc_tb)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 896, in __connect
       self.dbapi_connection = connection = pool._invoke_creator(self)
                                            ~~~~~~~~~~~~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/create.py",
 line 667, in connect
       return dialect.connect(*cargs_tup, **cparams)
              ~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/default.py",
 line 630, in connect
       return self.loaded_dbapi.connect(*cargs, **cparams)  # type: 
ignore[no-any-return]  # NOQA: E501
              ~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/psycopg2/__init__.py", line 
122, in connect
       conn = _connect(dsn, connection_factory=connection_factory, **kwasync)
   psycopg2.OperationalError: connection to server at 
"XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX.rds.amazonaws.com" (YYY.YY.YY.YYY), port 
5432 failed: fe_sendauth: no password supplied
   
   
   The above exception was the direct cause of the following exception:
   
   Traceback (most recent call last):
     File "/home/airflow/.local/bin/airflow", line 6, in <module>
       sys.exit(main())
                ~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/__main__.py", line 
61, in main
       args.func(args)
       ~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/cli_config.py", 
line 49, in command
       return func(*args, **kwargs)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/utils/cli.py", line 
113, in wrapper
       return f(*args, **kwargs)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/utils/providers_configuration_loader.py",
 line 54, in wrapped_function
       return func(*args, **kwargs)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/api_server_command.py",
 line 205, in wrapper
       return func(args)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/api_server_command.py",
 line 249, in api_server
       run_command_with_daemon_option(
       ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^
           args=args,
           ^^^^^^^^^^
       ...<7 lines>...
           ),
           ^^
       )
       ^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/daemon_utils.py",
 line 82, in run_command_with_daemon_option
       callback()
       ~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/api_server_command.py",
 line 252, in <lambda>
       callback=lambda: _run_api_server(
                        ~~~~~~~~~~~~~~~^
           args=args,
           ^^^^^^^^^^
       ...<3 lines>...
           proxy_headers=proxy_headers,
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^
       ),
       ^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/utils/memray_utils.py",
 line 61, in wrapper
       return func(*args, **kwargs)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/api_server_command.py",
 line 186, in _run_api_server
       run(
       ~~~^
           args=args,
           ^^^^^^^^^^
       ...<3 lines>...
           proxy_headers=proxy_headers,
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^
       )
       ^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/cli/commands/api_server_command.py",
 line 138, in _run_api_server_with_uvicorn
       uvicorn.run(
       ~~~~~~~~~~~^
           "airflow.api_fastapi.main:app",
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
           **uvicorn_kwargs,
           ^^^^^^^^^^^^^^^^^
       )
       ^
     File "/home/airflow/.local/lib/python3.14/site-packages/uvicorn/main.py", 
line 609, in run
       config.load_app()
       ~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/uvicorn/config.py", line 
428, in load_app
       return import_from_string(self.app)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/uvicorn/importer.py", line 
19, in import_from_string
       module = importlib.import_module(module_str)
     File "/usr/python/lib/python3.14/importlib/__init__.py", line 88, in 
import_module
       return _bootstrap._gcd_import(name[level:], package, level)
              ~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File "<frozen importlib._bootstrap>", line 1398, in _gcd_import
     File "<frozen importlib._bootstrap>", line 1371, in _find_and_load
     File "<frozen importlib._bootstrap>", line 1342, in _find_and_load_unlocked
     File "<frozen importlib._bootstrap>", line 938, in _load_unlocked
     File "<frozen importlib._bootstrap_external>", line 759, in exec_module
     File "<frozen importlib._bootstrap>", line 491, in 
_call_with_frames_removed
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/api_fastapi/main.py",
 line 46, in <module>
       app = cached_app(apps=os.environ.get("AIRFLOW_API_APPS", "all"))
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/api_fastapi/app.py", 
line 162, in cached_app
       return create_app(apps=apps)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/utils/providers_configuration_loader.py",
 line 54, in wrapped_function
       return func(*args, **kwargs)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/api_fastapi/app.py", 
line 148, in create_app
       init_auth_manager(app)
       ~~~~~~~~~~~~~~~~~^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/api_fastapi/app.py", 
line 205, in init_auth_manager
       if app and (auth_manager_fastapi_app := am.get_fastapi_app()):
                                               ~~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/providers/fab/auth_manager/fab_auth_manager.py",
 line 223, in get_fastapi_app
       flask_app = create_app(enable_plugins=False)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/providers/fab/www/app.py",
 line 130, in create_app
       init_airflow_session_interface(flask_app, db)
       ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/providers/fab/www/extensions/init_session.py",
 line 48, in init_airflow_session_interface
       app.session_interface = AirflowDatabaseSessionInterface(
                               ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^
           app=app,
           ^^^^^^^^
       ...<7 lines>...
           use_signer=True,
           ^^^^^^^^^^^^^^^^
       )
       ^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/airflow/providers/fab/www/session.py",
 line 62, in __init__
       super().__init__(*args, **kwargs)
       ~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/flask_session/sqlalchemy/sqlalchemy.py",
 line 112, in __init__
       self.sql_session_model.__table__.create(bind=engine, checkfirst=True)
       ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/sql/schema.py", 
line 1289, in create
       bind._run_ddl_visitor(ddl.SchemaGenerator, self, checkfirst=checkfirst)
       ~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 3269, in _run_ddl_visitor
       with self.begin() as conn:
            ~~~~~~~~~~^^
     File "/usr/python/lib/python3.14/contextlib.py", line 141, in __enter__
       return next(self.gen)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 3259, in begin
       with self.connect() as conn:
            ~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 3295, in connect
       return self._connection_cls(self)
              ~~~~~~~~~~~~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 146, in __init__
       Connection._handle_dbapi_exception_noconnection(
       ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^
           err, dialect, engine
           ^^^^^^^^^^^^^^^^^^^^
       )
       ^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 2450, in _handle_dbapi_exception_noconnection
       raise sqlalchemy_exception.with_traceback(exc_info[2]) from e
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 144, in __init__
       self._dbapi_connection = engine.raw_connection()
                                ~~~~~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/base.py", 
line 3319, in raw_connection
       return self.pool.connect()
              ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 448, in connect
       return _ConnectionFairy._checkout(self)
              ~~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 1272, in _checkout
       fairy = _ConnectionRecord.checkout(pool)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 712, in checkout
       rec = pool._do_get()
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/impl.py", 
line 178, in _do_get
       with util.safe_reraise():
            ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/util/langhelpers.py",
 line 122, in __exit__
       raise exc_value.with_traceback(exc_tb)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/impl.py", 
line 176, in _do_get
       return self._create_connection()
              ~~~~~~~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 389, in _create_connection
       return _ConnectionRecord(self)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 674, in __init__
       self.__connect()
       ~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 900, in __connect
       with util.safe_reraise():
            ~~~~~~~~~~~~~~~~~^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/util/langhelpers.py",
 line 122, in __exit__
       raise exc_value.with_traceback(exc_tb)
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/pool/base.py", 
line 896, in __connect
       self.dbapi_connection = connection = pool._invoke_creator(self)
                                            ~~~~~~~~~~~~~~~~~~~~^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/create.py",
 line 667, in connect
       return dialect.connect(*cargs_tup, **cparams)
              ~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/sqlalchemy/engine/default.py",
 line 630, in connect
       return self.loaded_dbapi.connect(*cargs, **cparams)  # type: 
ignore[no-any-return]  # NOQA: E501
              ~~~~~~~~~~~~~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^
     File 
"/home/airflow/.local/lib/python3.14/site-packages/psycopg2/__init__.py", line 
122, in connect
       conn = _connect(dsn, connection_factory=connection_factory, **kwasync)
   sqlalchemy.exc.OperationalError: (psycopg2.OperationalError) connection to 
server at "XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX.rds.amazonaws.com" 
(YYY.YY.YY.YYY), port 5432 failed: fe_sendauth: no password supplied
   
   (Background on this error at: https://sqlalche.me/e/20/e3q8)
   
   ```
   
   ### What you think should happen instead?
   
   _No response_
   
   ### Operating System
   
   _No response_
   
   ### Deployment
   
   None
   
   ### Apache Airflow Provider(s)
   
   _No response_
   
   ### Versions of Apache Airflow Providers
   
   _No response_
   
   ### Official Helm Chart version
   
   1.22.0 (latest released)
   
   ### Kubernetes Version
   
   1.36
   
   ### Helm Chart configuration
   
   _No response_
   
   ### Docker Image customizations
   
   _No response_
   
   ### Anything else?
   
   _No response_
   
   ### Are you willing to submit PR?
   
   - [ ] Yes I am willing to submit a PR!
   
   ### Code of Conduct
   
   - [x] I agree to follow this project's [Code of 
Conduct](https://github.com/apache/airflow/blob/main/CODE_OF_CONDUCT.md)
   


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