Venture capitalist says he almost had a heart attack after Claude AI deletes 15 years of family photos

man heart attack

• AI assistant accidentally deleted 15 years of family photos from user's desktop
• Apple support revealed hidden iCloud recovery, making files recoverable.
• Davidov warns against giving AI tools direct access to sensitive personal files

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A cautionary post by a venture capitalist is sparking fresh concerns about how much access people should give AI tools to their personal devices.

Nick Davidov, who is active in the tech and startup space, recently shared a detailed account on X describing a frightening experience with an AI assistant linked to Anthropic. His post quickly gained attention, not because of hype around AI, but because of what went wrong.

According to Davidov, he asked Claude Cowork, an AI tool designed to help with tasks, to organise his wife’s desktop files. At first, everything seemed normal. The AI began sorting files and even asked for permission to delete temporary Office files. Davidov agreed, assuming this was part of routine cleanup.

Then things took a sudden turn.

The AI reportedly responded with an “oops” message. It had tried to rename folders but instead ended up deleting a folder that contained nearly 15 years’ worth of photos. These were not just random pictures. The folder included family photos, images of their children growing up, artwork made by the kids, pictures from friends’ weddings, and memories from travels over the years.

What made the situation worse was that the deletion happened through the system terminal. This meant the files did not go to the trash. They were not backed up on an external drive, not saved on Time Machine, and iCloud had already synced the new folder structure. Even disk recovery tools could not detect the missing files.

Davidov described the moment as almost giving him a heart attack.

In a desperate attempt to recover the data, he contacted Apple. Apple support pointed him to a lesser-known feature in iCloud that allows users to recover files that were previously stored but are no longer on iCloud Drive. Apple keeps such files for up to 30 days.

That option turned out to be a lifesaver. Davidov said he watched as tens of thousands of files slowly began loading back, offering relief after what could have been a permanent loss.

In his post, Davidov issued a clear warning. He urged people not to give AI tools direct access to their actual file systems, especially when the data is difficult or impossible to replace. He added that tools like Claude Cowork and Claude Code are not yet ready for everyday use in sensitive environments.

The incident highlights a growing issue as AI tools become more powerful and more deeply integrated into daily workflows. While they promise convenience, Davidov’s experience is a reminder that when things go wrong, the cost can be deeply personal.