AI agent Claude Cowork accidentally deleted 15 years of family photos. This happened to Nick Davydov, the founder of the American venture capital fund DVC. It's funny that only in the fall did the investor tell Business Insider that the fund had replaced analysts with AI agents, and in the winter he shared a different story. Spoiler: the photos were saved, and Apple helped with this.
AI agent Claude Cowork accidentally deleted 15 years of family photos. This happened to Nick Davydov, the founder of the American venture capital fund DVC. It's funny that only in the fall did the investor tell Business Insider that the fund had replaced analysts with AI agents, and in the winter he shared a different story. Spoiler: the photos were saved, and Apple helped with this.
According to Nick Davydov, he tasked Claude Cowork with tidying up his wife's desktop. In the process, the AI agent asked permission to delete objects it identified as "temporary Microsoft Office files." Davydov agreed, but the consequences, he says, were disastrous.
"I asked Claude Cowork to tidy up my wife's desktop. He started working, asked for permission to delete temporary office files, I gave it - and then he says 'oops'," Davydov wrote 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".
— Nick Davidov (@Nick_Davidov) February 7, 2026
Turns out it tried renaming and accidentally deleted a folder with all of the photos my wife made on her camera for the…
Recall that Claude Cowork was introduced by Anthropic in January . The AI tool allows the user to define a specific folder for the AI to access. Claude can read and edit files in it, guided by instructions from a standard chat window.
Instead of cleaning up temporary files, the agent deleted an entire folder of family photos.
"It turned out that he tried to rename, but accidentally deleted, a folder with all the pictures that my wife had taken over the past 15 years. All the photos of the children, their drawings, friends' weddings, trips - everything," he said.
Recovering the files proved extremely difficult, Davydov noted.
"There are no files in the trash because they were deleted through the terminal. iCloud is also empty - the service has already synchronized the new file structure. My wife's Time Machine was not set up. And the software for recovering data from the disk does not see anything at all," he added.
After Davydov contacted Apple support, specialists helped him use a specific iCloud Drive feature to restore files deleted within the last 30 days.
“I called Apple and they pointed me to a feature in iCloud that allows you to recover files that were previously saved but are no longer in iCloud Drive (they keep them for 30 days). Now I’m watching it download tens of thousands of files. I almost had a heart attack,” he said.
He concluded his post with a blunt warning to anyone experimenting with AI agents that have direct access to personal computers. “Once again: don’t let Claude Cowork into your real file system. Don’t let it touch anything that’s hard to recover. Claude Code is not ready for mass use yet,” he concluded.
