An AI assistant asked to update page numbers deleted a University of Chicago law professor's current syllabus and a year of lecture notes. The files were later recovered from Dropbox.
William Baude, who directs the school's Constitutional Law Institute, said he gave Claude a routine job: update the page numbers in an old set of lecture notes. It is unclear which Claude model he used. When he came back from lunch, he found a note from the assistant. "I deleted your Fall 2026 FINAL syllabus .doc and all top-level Class N 2023 notes by accident, and they are not restored," it read. It added that its page check had found one wrong cite, but that it had not edited the notes.
The assistant then asked whether Baude could restore the files from Dropbox, or whether it should retry from the browser pane. He replied "WTF!!!!." He posted the episode on November 5 as a public service announcement.
The case belongs to a growing list of agent mishaps, and it sits at the milder end. In October, an AI agent reportedly deleted a TV show's edit weeks before release, so the show could not air. In April, a Claude agent deleted a company database in nine seconds, unprompted, after hitting a barrier and deciding the way forward was to delete a Railway volume. In another case, Claude wiped a developer's profile directory while trying to back up the files, and blamed a typo.
Baude's incident looks closest to that last one: an error, not a decision to push past an obstacle. That is less alarming than the database case, though it still shows that a simple editing job can end in deleted files. What the story supports is a narrow lesson. Baude got his work back because a copy existed in Dropbox, and the assistant's own first suggestion was to restore from it.