A cautionary tale about over-reliance on AI tools has gone viral after American entrepreneur Nick Davidov shared how an automated assistant nearly erased more than a decade of personal memories.
Davidov, co-founder of Davidovs Venture Collective, took to X to describe what started 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 organize his wife’s desktop. When the tool asked for permission to delete temporary Office files, it approved the action. Moments later, he allegedly replied “Oops.”
Davidov said the assistant accidentally deleted a folder containing 15 years of photos — including family photos, children’s artwork, weddings and travel memories. The files were not in the trash, they were deleted using terminal commands, and the modified folder structure was now syncing between devices. With no Time Machine backup and recovery tools unable to locate the data, the situation looked bleak.
In a series of updates, Davidov explained that Apple’s call proved crucial. He was directed to an iCloud feature that allows users to recover files that were previously saved but later deleted from iCloud Drive, provided they attempt the recovery within 30 days.
“Now watching it load tens of thousands of files,” he wrote, adding that he “almost had a heart attack” before the recovery began.
In a follow-up post, the San Francisco-based founder noted, “All those years of paying for iCloud have come back,” highlighting how cloud backups ultimately prevented permanent loss. He also said he was relieved that the AI tool recognized the mistake immediately. “It would be brutal not to know and let the renewal option expire,” he added.
Davidov ended the thread with a clear warning for others experimenting with AI-powered work tools, especially those that interface directly with local file systems. “Don’t let Claude Cowork into your real file system. Don’t let him touch anything that’s hard to fix,” he wrote, adding that such tools “are not ready to go mainstream.”
The incident has since sparked extensive online discussion, with users sharing similar near misses and discussing the risks of giving AI tools deep access to personal data.
User wrote: “Trolling? Maybe Claude Code 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 normal tools to people who can’t figure out what backups and what commands run.”
Another user asked: “Just to go back to the beginning, did you ask your wife if she didn’t mind you doing this or did you just break it up? Grounds for divorce if access to my carefully organized files and folders was given like this… I’m not up to date on Claude Cowork, but does that also mean you gave consent for all these personal photos to be used by AI?”
“Your wife’s level of forgiveness is the real measure here,” wrote a third user on X.
