The operator's 500 was NOT the startup gap I attributed it to. They found it by logging in and getting Steward's own error page -- which means create_app had completed and the app was serving, so the gaierror came from a request handler acquiring a connection, not from boot. Neither prior fix covers that: the startup retry never runs, and pool_pre_ping only helps once the database is back, since its replacement connect fails too while the container is gone. Adds a before_request gate that acquires a pooled connection with a short bounded retry (~1.75s over 4 tries) so a database restart is ridden out invisibly, and renders a distinct 503 "database unavailable" page when the budget is exhausted. The request budget is deliberately far shorter than the startup one: nobody watches a container boot, but somebody is watching this page load, and a page that hangs is worse than one that says what is wrong. /health and static are exempt -- a liveness probe must stay answerable while the database is down, or a dependency outage triggers a restart loop. Credential and missing-database errors still propagate rather than being reported as "unavailable", which would send the operator chasing the wrong problem entirely. Co-Authored-By: Claude Opus 5 <noreply@anthropic.com>