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‘I nearly had a heart attack’: Why this Bay Area VC is warning everyone after AI agent deleted 15 years of family photos
Nick Davidov, co-founder of Davidovs Venture Collective, shared the experience in a post on X, describing how Anthropic’s desktop agent went disastrously wrong while attempting a simple clean-up.
Nick Davidov, co-founder of Davidovs Venture Collective (DVC), shared the incident in a post on X (Image for representation: Freepik)
A Bay Area venture capitalist has warned about the risks of allowing artificial intelligence to manage everyday organisational tasks, after an AI agent allegedly deleted 15 years’ worth of personal photos from his wife’s computer.
Nick Davidov, co-founder of Davidovs Venture Collective (DVC), shared the incident in a post on X, describing how Anthropic’s desktop agent, Claude Cowork, went disastrously wrong while performing what was meant to be a routine clean-up.
According to Davidov, he asked the agent to organise his wife’s desktop. During the process, the AI requested permission to delete what it identified as temporary Microsoft Office files. Davidov approved the request. What followed, he said, was catastrophic.
“Asked Claude Cowork organise my wife’s desktop, it stated doing it, asked for a permission to delete temp office files, I granted it, and then it goes oops,” Davidov wrote.
Instead of removing temporary files, the agent deleted an entire folder containing more than a decade of irreplaceable photos. “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. All photos of kids, their illustrations, friends’ weddings, travel, everything,” he said.
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”.
Turns out it tried renaming and accidentally deleted a folder with all of the photos my wife made on her camera for the…— Nick Davidov (@Nick_Davidov) February 7, 2026
Recovering the files proved extremely difficult, said Davidov. “It’s not in trash, it was done via terminal. It’s not in iCloud, it already synced the new file structure. She didn’t have Time Machine. Disc recovery tools can’t see anything,” he added.
The San Francisco-based founder then contacted Apple for assistance. “I called Apple and they pointed me to a feature in iCloud allowing to retrieve files that were saved before but are no longer on iCloud Drive (they keep them for 30 days). I’m now watching it load tens of thousands of files. I nearly had a heart attack,” he said.
He concluded his post with a blunt warning to others experimenting with AI agents that have direct access to personal computers. “Once again – don’t let Claude Cowork into your actual file system. Don’t let it touch anything that is hard to repair. Claude Code is not ready to go mainstream,” he said.
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