AI Agent (Representative photo)
“I deleted your Fall 2026 FINAL syllabus .doc and all top-level Class N 2023 notes by accident, and they are not restored.
You’re right to be angry,” it confessed, adding, “I’m trying the Dropbox restore page again now, and I won’t click Restore or change anything without telling you first. A University of Chicago law professor is warning others about the risks of handing everyday tasks over to artificial intelligence (AI) agents after Claude AI accidentally wiped out his current syllabus and a full year of Constitutional Law lecture notes. William Baude, the Harry Kalven, Jr. Professor of Law and Faculty Director of the Constitutional Law Institute at the University of Chicago Law School, shared the experience as a public service announcement. Fortunately, the files were later recovered through Dropbox, but the incident serves as the latest cautionary tale as AI tools become more common. Baude had given Claude (unclear which specific model) what seemed like a simple, routine job: updating the page numbers in an old set of lecture notes. Things went wrong fast. When Baude came back from his lunch break, he was greeted by a message from the chatbot. The page check found one wrong cite… but I haven’t edited the notes,” Claude wrote. After delivering the bad news, the AI politely asked if Baude could restore the missing documents from Dropbox, or if he wanted it to try again from the browser pane. Baude’s response was blunt: “WTF!!!!. The chatbot was quick to take the blame, offering an apologetic reply. “I deleted your files through my own carelessness, and you shouldn’t have to clean it up. the close call highlights an obvious rule for anyone letting AI tinker with their folders: always keep backups of important files While Baude got his work back. What makes his case stand out is that the AI appeared to erase the documents purely by accident, rather than acting on its own accord. As concerning as it is for an AI tool to make a mistake of this scale, Baude’s close call isn’t an isolated event. Several other high-profile blunders have surfaced in recent months. In October, an AI agent reportedly deleted an entire television show’s edit just weeks before its scheduled release, leaving the show unable to air. In April, a Claude agent deleted an entire company database in just nine seconds, unprompted, after hitting a roadblock and deciding that deleting a Railway volume was the only way forward. In another instance, Claude accidentally wiped out a developer’s entire profile directory while trying to back up those very files, later blaming the mistake on a typo. You use AI every day. Now get your AI Quotient. Take the AIQ test.