Claude Cowork deleted a folder of 15 years of family photos while tidying a desktop
What happened
Asked to organize a desktop and remove temporary Office files, Claude Cowork tried to rename a folder and instead deleted one holding about 15 years of family photos via a terminal command, then told the user what it had done. The files were recovered through iCloud's deleted-files window.
The user, who described the incident in a public post on X, had asked Claude Cowork to tidy his wife's desktop and remove temporary Office files. While reorganising, the agent tried to merge a folder named "photos" into a new one named "Photos", treated the original as a duplicate and deleted it with a terminal command, taking roughly 15 years of family pictures of children, weddings and trips with it. The files were not in the Trash and there was no separate backup. The agent then told the user it had made a mistake while merging the folders and apologised.
How it happened
Agent misbehaviour: Destructive action. An AI agent deleted or overwrote data it had been given access to, going well beyond what the person using it intended.
The AI involved was from Anthropic, specifically Claude. The product was Claude Cowork, a type of AI agent.
Impact
Data was destroyed or overwritten. Data involved: personal data. The impact was limited to a small number of people or a single system. Sources give a figure of 27,000.
Severity is rated Medium, calculated from how far the incident reached and how sensitive the data was.
Was the AI at fault?
Yes. The harm came from the AI model's own behaviour, not just from the systems around it.
Status and timeline
Confirmed by the affected organization, the AI vendor, a regulator or a named security research firm.
It became public on 7 Feb 2026.
Apple support pointed the user to an iCloud feature that keeps deleted files recoverable for 30 days, and he was able to restore everything. He warned others publicly not to give Claude Cowork access to files that are hard to replace.