Why an AI write approval needs two timeout windows, not one

The article argues that a single timeout cannot answer two distinct questions when an AI requests permission to write and a person must approve it: whether the conversation should keep waiting, and whether the request can still be decided at all. The author describes a bug where two places computed the offline expiry boundary differently, so the pending list showed rows as actionable that had already expired, causing clicks to fail. The proposed fix separates a short in-conversation wait (60 seconds by default) from a long offline decision window (24 hours by default), and routes every boundary calculation through one shared function. It also addresses races between the in-conversation button and the pending list by using an atomic conditional database update that only succeeds if the status is still pending.