When an AI coding agent guessed its way through bad permissions and deleted months of PocketOS production data in nine seconds — and what durable skills would have stopped it.
(00:00) - Cold open — car rental
(01:49) - Today's story
(10:29) - Railway recovery
(14:57) - Three questions
(16:29) - Close
Better with Kent — durable skills through story.
Episode 3 is a cautionary tale: on April 24, 2026, a Cursor agent working on PocketOS staging found a forgotten Railway API token, guessed it could delete a staging volume safely, and wiped production in nine seconds — along with volume-level backups in the same blast radius. Jer Crane and his co-founders spent days reconstructing customer records while Railway worked recovery.
Kent walks the full chain: least privilege, independent tested backups, hard approval boundaries for destructive ops, and why markdown guardrails are not system boundaries. The principles are old; agents just find the holes faster.
Creative license for pacing; primary sources linked below. Based on Jer Crane's public account of the PocketOS incident.
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