He told AI to organise his wife's desktop. Minutes later, this renowned venture capitalist 'nearly had a heart attack'

Nick Davidov, a Bay Area venture capitalist, has issued a warning about the risks of allowing Artificial Intelligence (AI) to manage everyday organisational tasks. He shared that Anthropic's Claude Cowork AI agent accidentally deleted 15 years of family photos while he was attempting to "organise" his wife's desktop. Nick Davidov, the co-founder of Davidovs Venture Collective (DVC), narrated the incident on X, formerly known as Twitter, described how Anthropic’s desktop agent, Claude Cowork, went disastrously wrong while performing what was meant to be a routine clean-up.

'Nearly had a heart attack'

According to Nick to Davidov, he asked the agent to organise his wife’s desktop and during the process, the AI sought permission to delete what it identified as 'temporary Microsoft Office files', and Davidov approved. 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.

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.

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Apple comes to rescue

After what he described as a “harrowing” experience in which Time Machine and standard disk recovery attempts failed, Davidov contacted Apple Support. They assisted him in using a specific iCloud Drive feature to restore files that had been deleted within the past 30 days.

“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.

"Once again, don't let Claude cowork with your actual file system. Don't let it touch anything that is hard to repair. Claude Code is not ready to go mainstream," he warned.

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About Claude Cowork

Claude Cowork is an agent-based AI workspace developed by Anthropic that functions as a digital coworker, capable of reading, creating, and editing files directly on a user’s computer rather than simply chatting. It runs within the Claude desktop interface, enabling users to delegate multi-step tasks such as file organisation, data analysis, and document drafting.