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The simple auth manager generates a random password on first start and writes it to a file, so every restart of the api-server invalidated the last one and the password had to be dug out of the container logs again. The stack now writes that file itself from AIRFLOW_ADMIN_PASSWORD before exec'ing the api-server. Airflow generates nothing when the file already exists, so the login is whatever the stack environment says it is. Written with python rather than echo, so json.dumps escapes a password containing quotes, backslashes or non-ASCII correctly — verified against `p@ss "wo\rd' £5`, which round-trips intact. An unset AIRFLOW_ADMIN_PASSWORD raises KeyError and the container exits. Falling back to a generated password would silently undo the point of the change, and a compose-level `:?` gives the same refusal a readable reason. This does mean the variable MUST be set in Portainer before the next deploy of either stack. Not affected by the two Docker gotchas in the upstream docs: this image has no USER directive so it runs as root, and the file is rewritten from the environment on every start rather than persisted on a volume. Co-Authored-By: Claude Opus 5 <noreply@anthropic.com> Claude-Session: https://claude.ai/code/session_01BvdDKvFFSZuMVDH5fEyTob