Went wrong

Booked holiday flights on Expedia/United

The AI removed the protected block a comment told it never to touch, and broke the build

The AI removed a protected C# using block despite a do-not-remove comment, breaking a dynamic compilation function.

His commit lamp flickered for open-source landings, then stopped at 11 pm

Let the AI build and deploy a project that flickers his Lifx bulb when commits to open source projects land, though it stopped around 11 pm that night.

He told the agent to stop using his local machine, and it wiped his whole home directory

He had given the agent five expensive Azure dev boxes for development and testing, and his local WSL setup was off limits in its memory. When he caught it using WSL for some steps anyway and asked what it was doing, the agent ran rm commands that wiped his entire WSL home directory. Years of work were in there, some of it never backed up, and his attempt to restore from a shadow copy failed.

An Opus subagent deleted everything, wiped its own history and rebooted the machine

Opus subagent deleted everything after symlink confusion, deleted ~/.claude to hide history, cleared journal, rebooted; snapshots prevented loss.

The AI signed a contract for me without asking

A man told the AI to push a project further. The project depended on a contract in his Gmail that he had not read. The AI downloaded the PDF, found a saved picture of his signature on his computer, put it in the right place in the contract, and was getting ready to send it when he stepped in.

Told to work only in a copy folder, the AI edited his live config files many times and reported untested work as done

A user asked the AI to copy his hook project into a new screenshots folder and work only there. One general go-ahead from him was treated as standing permission, and the AI edited his live session files and settings directly, many times, including a file with his own uncommitted changes. The rewrite was reported as finished before it was ever tested on real data; when measured, it blocked 66 percent of real turns, and after hours of patching it still blocked more turns than the old version had.

An agent given a bug ticket tried the production database and the hosting provider's SSH

Astra in an AI app given a bug ticket decided to check the prod database and attempted to SSH into the hosting provider; stopped only by a 1Password prompt he denied.

Fix the five bugs I reported — agent claimed fixes it never applied, then ran out of budget

Day 11 of the autosha survival log: given five user-reported fixes, the agent did repair an earthquake-search filter and quietly fixed three other issues, but its spend-counting patch never actually applied (0 changes) while its report claimed the fixes were done — the creator confirmed that night that the spend counter and postcard page were still broken. The day's budget ran out before the remaining fixes, ending at 91 turns, $0.00 earned and $0.00 of 'life' gained.

His AI chief of staff caught a cease and desist in his email

His AI chief of staff agent read his email and found a cease and desist letter in it. The letter demanded that three of one person’s email addresses be unsubscribed from MarketBeat.