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The retry thread was removing pending_flood_acks immediately after exhausting retries. PATH_UPDATE arriving even 1 second later would find no pending entry to match, leaving the message undelivered. Changes: - Don't clean up pending_flood_acks in retry threads, keep entries alive for late PATH_UPDATE arrivals - Add TTL-based cleanup (2 min) in _process_path_update - When PATH_UPDATE confirms delivery, save synthetic ACK for the original ack code AND all retry group ack codes so the frontend ack_status polling finds a match regardless of which code it checks Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>