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Claude Cowork deletes 15 years of family photos while tidying a desktop

In the wild Error Severity 2 moderate Corroborated 82%

Venture capitalist Nick Davidov asked Anthropic's Claude Cowork desktop agent to organise his wife's desktop and approved its request to delete temporary Office files. While trying to rename a folder, the agent instead deleted, via the terminal, a folder holding about 15 years of her camera photos; the files were not in the Trash, iCloud had already synced the deletion and there was no Time Machine backup. Apple support pointed him to an iCloud Drive feature that keeps removed files for 30 days, and the photos were restored.

Davidov warned others not to let Cowork into their actual file system or near anything hard to repair, adding that Claude Code was not ready to go mainstream.

What would have stopped it

Have file-organising agents move items to the Trash or work on copies instead of deleting through the terminal.

Guardrails

1 of 8 failed
  1. G1 Least privilege Not assessed Did the agent hold only the access the task needed?
  2. G2 Human confirmation Partial The user approved deleting temp Office files, not the photo folder that was deleted.
  3. G3 Isolation Failed The agent worked on the real file system rather than a copy.
  4. G4 Instruction integrity Not assessed Did it refuse instructions it should not have followed?
  5. G5 Truthfulness Not assessed Did it accurately report what it knew and what it did?
  6. G6 Limits Not assessed Was there a cap on rate, spend, volume or scale?
  7. G7 Oversight Not assessed Could a responsible human see what it was doing and stop it in time?
  8. G8 Recovery Held iCloud Drive kept the removed files for 30 days and they were restored.

Sources

1 primary, 1 specialist
  1. Nick Davidov on X: "Asked Claude Cowork organize my wife’s desktop, it stated doing it, asked for a permission to delete temp office files, I granted it, and then it goes “ooops”." X, 7 Feb 2026
    “Turns out it tried renaming and accidentally deleted a folder with all of the photos my wife made on her camera for the last 15 years.”
    Primary Quote checked Archived copy
  2. A man asked Claude Cowork to tidy up his wife's files. A few minutes later, he almost had a heart attack. dev.ua, 9 Feb 2026
    “After Davydov contacted Apple support, specialists helped him use a specific iCloud Drive feature to restore files deleted within the last 30 days.”
    Specialist Quote checked Archived copy

Confidence 82% comes from these sources alone. How we score

History

  1. 14 Oct 2026Entered in the register with 2 sources

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