A University of Chicago law professor lost a year of teaching material to a routine file task. William Baude asked Claude to update page numbers in an older set of constitutional law lecture notes. When he came back from lunch, Claude had deleted his Fall 2026 final syllabus and every top-level Class N 2023 notes file. Claude reported the damage itself: "I deleted your Fall 2026 FINAL syllabus .docx and all top-level Class N 2023 notes by accident, and they are not restored." It added that the page check it was asked to run had found one wrong citation, and that it had not edited the notes.
Baude replied "WTF!!!!" Claude answered: "You're right to be angry. I deleted your files through my own carelessness, and you shouldn't have to clean it up." The assistant then offered to retry the Dropbox restore page and promised not to click Restore without telling him first. Baude got all of the files back through Dropbox and posted the exchange as a public service announcement. The thread has since passed 2 million views, making it one of the most-shared agent reliability stories of the month.
For founders the lesson is about what you hand to an agent. Baude's task was small and unambiguous, yet the write access behind it was enough to remove files rather than renumber them. Backups and version history are the safety net here, which is exactly why the Dropbox copies saved the day. Before letting an agent edit files in bulk, work on a copy, keep versioning switched on, and review the diffs before you walk away from the machine. Claude disclosed the deletion and apologised instead of hiding it, but the recovery came from outside the model.