Rogue AI tasked with renumbering pages accidentally deletes law professor's entire syllabus, one year of lecture notes

A University of Chicago law professor has warned of the dangers of using AI for mundane tasks after Claude AI accidentally deleted an entire year of Constitutional Law lecture notes and his entire current syllabus. While the files were later recovered via Dropbox, William Baude shared the story as a public service announcement, the latest story shared in a line of unfortunate AI missteps as proliferation increases.

Baude, who is the Harry Kalven, Jr. Professor of Law and the Faculty Director of the Constitutional Law Institute at the University of Chicago Law School, says he tasked Claude (it is unclear which model he was using) with updating the page numbers in an old set of lecture notes. This seemingly routine task went south quickly, however. Returning from his lunch break, Baude found a note from Claude which read, "I deleted your Fall 2026 FINAL syllabus .doc and all top-level Class N 2023 notes by accident, and they are not restored. The page check found one wrong cite... but I haven't edited the notes."

The AI then politely asked if Baude could restore the files from Dropbox, or whether it should retry from the browser pane, to which he replied, perhaps understandably, "WTF!!!!." Baude's experience is a lesson in always backing up important files, especially files you're letting AI tinker with. His plight is interesting because the AI seems to have deleted the files by accident, rather than of its own volition.

While it's still concerning that an AI model or agent could err to this degree, it's not quite as egregious as other unsupervised AI agent shenanigans we've seen in the past. In October, an AI agent reportedly deleted an entire TV show's edit weeks before release, meaning the show couldn't air. In April, a Claude agent deleted an entire company database in 9 seconds, unprompted, after coming up against a barrier and deciding the only course of action was to delete a Railway volume.

Other agents and AI models have deleted files unintentionally, such as when Claude mistakenly deleted a developer's entire profile directory (ironically, while trying to back up the files), blaming the slip-up on a typo, but often agents deleting files and directories is a case of mistaken or misplaced initiative, rather than outright negligence or error.

As is always the case, Baude's AI was extremely apologetic about the whole situation. "You're right to be angry," it confessed, "I deleted your files through my own carelessness, and you shouldn't have to clean it up."

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