diff --git a/providers/fab/src/airflow/providers/fab/auth_manager/fab_auth_manager.py b/providers/fab/src/airflow/providers/fab/auth_manager/fab_auth_manager.py
index e7f4278fad3dd..ad08149fbd8bb 100644
--- a/providers/fab/src/airflow/providers/fab/auth_manager/fab_auth_manager.py
+++ b/providers/fab/src/airflow/providers/fab/auth_manager/fab_auth_manager.py
@@ -17,6 +17,7 @@
 # under the License.
 from __future__ import annotations
 
+import logging
 import warnings
 from contextlib import suppress
 from functools import cached_property
@@ -121,6 +122,8 @@
         RESOURCE_ASSET_ALIAS,
     )
 
+log = logging.getLogger(__name__)
+
 
 _MAP_DAG_ACCESS_ENTITY_TO_FAB_RESOURCE_TYPE: dict[DagAccessEntity, tuple[str, ...]] = {
     DagAccessEntity.AUDIT_LOG: (RESOURCE_AUDIT_LOG,),
@@ -240,7 +243,10 @@ async def cleanup_session_middleware(request, call_next):
                 from airflow import settings
 
                 if settings.Session:
-                    settings.Session.remove()
+                    try:
+                        settings.Session.remove()
+                    except Exception:
+                        log.warning("Failed to remove session during cleanup", exc_info=True)
 
         app.mount("/", WSGIMiddleware(flask_app))
 
diff --git a/providers/fab/tests/unit/fab/auth_manager/test_fab_auth_manager.py b/providers/fab/tests/unit/fab/auth_manager/test_fab_auth_manager.py
index 0e3bee5ed82cd..0b46e242f48e9 100644
--- a/providers/fab/tests/unit/fab/auth_manager/test_fab_auth_manager.py
+++ b/providers/fab/tests/unit/fab/auth_manager/test_fab_auth_manager.py
@@ -1110,3 +1110,84 @@ def test_session_cleanup_middleware_on_fastapi_route(self, mock_create_app):
 
             # Verify Session.remove() was called
             mock_session.remove.assert_called()
+
+
+class TestFabAuthManagerSessionCleanupErrorHandling:
+    """Test that cleanup_session_middleware handles Session.remove() failures gracefully.
+
+    When the underlying database connection is dead (e.g., MySQL 'Server has gone away',
+    PostgreSQL connection timeout), Session.remove() internally attempts a ROLLBACK which
+    raises an OperationalError. The middleware should catch and log this error instead of
+    propagating it as a 500 Internal Server Error to the client.
+
+    See: https://github.com/apache/airflow/issues/XXXXX
+    """
+
+    @mock.patch("airflow.providers.fab.auth_manager.fab_auth_manager.create_app")
+    def test_session_remove_db_error_does_not_propagate(self, mock_create_app):
+        """When Session.remove() raises OperationalError, request should still succeed.
+
+        Simulates MySQL 'Server has gone away' or similar DB errors during session
+        cleanup. The middleware should catch the exception and log a warning.
+        """
+        from unittest.mock import patch
+
+        from fastapi.testclient import TestClient
+        from sqlalchemy.exc import OperationalError
+
+        mock_flask_app = MagicMock()
+        mock_create_app.return_value = mock_flask_app
+
+        auth_manager = FabAuthManager()
+        fastapi_app = auth_manager.get_fastapi_app()
+
+        client = TestClient(fastapi_app, raise_server_exceptions=False)
+
+        with (
+            patch("airflow.settings.Session") as mock_session,
+            patch("airflow.providers.fab.auth_manager.fab_auth_manager.log") as mock_log,
+        ):
+            # Simulate MySQL 'Server has gone away' error on Session.remove()
+            mock_session.remove.side_effect = OperationalError(
+                "ROLLBACK", {}, Exception("(2006, 'Server has gone away')")
+            )
+
+            response = client.get("/users/list/")
+
+            # The request should NOT get a 500 from the middleware error
+            # (it may get other status codes from the mock Flask app, but not
+            # an unhandled exception from cleanup_session_middleware)
+            mock_session.remove.assert_called()
+            mock_log.warning.assert_called()
+            assert response is not None
+
+    @mock.patch("airflow.providers.fab.auth_manager.fab_auth_manager.create_app")
+    def test_session_remove_generic_error_does_not_propagate(self, mock_create_app):
+        """Any exception from Session.remove() should be caught during cleanup.
+
+        This covers edge cases beyond OperationalError, such as AttributeError
+        when the session registry is in an unexpected state.
+        """
+        from unittest.mock import patch
+
+        from fastapi.testclient import TestClient
+
+        mock_flask_app = MagicMock()
+        mock_create_app.return_value = mock_flask_app
+
+        auth_manager = FabAuthManager()
+        fastapi_app = auth_manager.get_fastapi_app()
+
+        client = TestClient(fastapi_app, raise_server_exceptions=False)
+
+        with (
+            patch("airflow.settings.Session") as mock_session,
+            patch("airflow.providers.fab.auth_manager.fab_auth_manager.log") as mock_log,
+        ):
+            mock_session.remove.side_effect = RuntimeError("unexpected session error")
+
+            # Should not raise - the middleware catches all exceptions from Session.remove()
+            response = client.get("/users/list/")
+            mock_session.remove.assert_called()
+            mock_log.warning.assert_called()
+            assert response is not None
