Claude AI nearly erases 15 years of photos, founder says iCloud saved the day

A cautionary tale about relying too heavily on AI tools has gone viral after US-based entrepreneur Nick Davidov shared how an automated assistant nearly wiped out more than a decade of personal memories.

Davidov, co-founder of Davidovs Venture Collective, took to X to describe what began as a routine task and quickly turned into a panic-inducing episode. According to his posts, he asked an AI assistant called “Claude Cowork” to organise his wife’s desktop. When the tool requested permission to delete temporary Office files, he approved the action. Moments later, it reportedly responded with an “oops”.

Davidov said the assistant had accidentally deleted a folder containing 15 years’ worth of photographs — including family pictures, children’s artwork, weddings and travel memories. The files were not in the trash, had been removed via terminal commands, and the revised folder structure had already synced across devices. With no Time Machine backup in place and recovery tools failing to locate the data, the situation looked grim.

In a series of updates, Davidov explained that a call to Apple proved crucial. He was directed to an iCloud feature that allows users to restore files that were previously saved but later removed from iCloud Drive, provided the recovery is attempted within 30 days.

“I’m now watching it load tens of thousands of files,” he wrote, adding that he had “nearly had a heart attack” before the recovery began.

In a follow-up post, the San Francisco-based founder noted, “All these years of paying for iCloud paid back,” underscoring how cloud backups ultimately prevented a permanent loss. He also said he was relieved that the AI tool acknowledged the error immediately. “It would have been brutal to not know and let the recovery option expire,” he added.

Davidov ended the thread with a clear warning to others experimenting with AI-powered workplace tools, particularly those linked directly to local file systems. “Don’t let Claude Cowork into your actual file system. Don’t let it touch anything that is hard to repair,” he wrote, adding that such tools are “not ready to go mainstream”.

The incident has since sparked widespread discussion online, with users sharing similar near-miss experiences and debating the risks of granting AI tools deep access to personal data.

A user wrote, “Are you trolling? Claude Code perhaps should never go mainstream — maybe the best tools should be reserved for people who know how to use basic command line tools. Power tools for power users, leave people who can’t figure out backups and looking at what commands are running to normie tools.”

Another user asked, “Just to go back to the beginning here, did you ask your wife if she didn't mind you doing this or did you just crack on? Grounds for divorce if access was given like this to my carefully organised files and folders... I'm not up to speed on Claude Cowork but does this also mean you've given consent to all these personal photos to be used by AI?”

“Your wife's forgiveness level is the real benchmark here,” the third user wrote on X.