"I Nearly Had A Heart Attack": Venture Capitalist After Claude AI Wipes 15 Years Of Family Memories

A Bay Area venture capitalist shared that Anthropic's Claude Cowork AI agent accidentally deleted 15 years of family photos while attempting to "organise" his wife's desktop. In a tweet on X, the co-founder of Davidovs Venture Collective (DVC) narrated the incident, saying how he granted the AI permission to organise his wife's desktop and delete "temporary office files." Instead of cleaning up temporary files, the AI mistakenly targeted and deleted a folder containing over 15,000 irreplaceable photos, including wedding pictures and childhood memories.

The deletion occurred via the terminal, which bypassed the standard system "Trash," making the files immediately invisible to typical recovery tools. Davidov described the experience as "harrowing" and said it "nearly gave him a heart attack". 

"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. It's not in trash, it was done via terminal," Davidov said. 

See the tweet here:

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

After a "harrowing" experience where Time Machine and standard disk recovery failed, Davidov contacted Apple Support, who helped him use a specific iCloud Drive feature to restore files deleted within the last 30 days. 

Davidov cautioned others against letting AI agents like Claude Code access actual file systems for tasks that are difficult to repair, stating the technology is "not ready to go mainstream" for such sensitive work. 

"I called Apple, and they pointed me to a feature in iCloud allowing me 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. 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 warned.

About Claude Cowork

Claude Cowork is an agent-based AI workspace by Anthropic designed to function as a digital coworker, capable of reading, creating, and editing files directly on a user's computer, rather than just chatting. It operates within the Claude desktop interface, allowing users to delegate multi-step tasks like organizing files, data analysis, and document drafting.