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Claude asked to renumber pages deletes professor's syllabus, year of notes

Original text(via Hacker News)
Claude
Claude

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.

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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."

Yesterday while I was at lunch, Claude deleted a year of con law lecture notes and my current syllabus. https://t.co/o3XB8UiugkNovember 5, 2026

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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Stephen Warwick
Stephen Warwick

Stephen is Tom's Hardware's News Editor with almost a decade of industry experience covering technology, having worked at TechRadar, iMore, and even Apple over the years. He has covered the world of consumer tech from nearly every angle, including supply chain rumors, patents, and litigation, and more. When he's not at work, he loves reading about history and playing video games.

  • Anyone who reads this article and, still doesn't backup important files, you are an idiot... Reply
  • Altman: introducing Ai Backup. Getting tired of ai agents deleting your stuff? We got you fam, our new cloud backup system automatically backs up everything before one of our agents "accidentally" deletes it... Reply
  • Dementoss said:Anyone who reads this article and, still doesn't backup important files, you are an idiot... While true and the headline seemingly purposely avoids mentioning it, the article does say the files were recovered through Dropbox. Not my preferred backup method, but it's something. My guess is the headline omitted this to make the non-story more sensational. Reply
Dementoss said:Anyone who reads this article and, still doesn't backup important files, you are an idiot...
  • Thunder64 said:While true and the headline seemingly purposely avoids mentioning it, the article does say the files were recovered through Dropbox. Not my preferred backup method, but it's something. My guess is the headline omitted this to make the non-story more sensational.Yes, I did read that first before typing. If it gets more people taking backing up seriously, then the article is worthwhile. Reply
Thunder64 said:While true and the headline seemingly purposely avoids mentioning it, the article does say the files were recovered through Dropbox. Not my preferred backup method, but it's something. My guess is the headline omitted this to make the non-story more sensational.
  • S58_is_the_goat said:Altman: introducing Ai Backup. Getting tired of ai agents deleting your stuff? We got you fam, our new cloud backup system automatically backs up everything before one of our agents "accidentally" deletes it...until the ai think you aren't current on subscription and delete the backup. Reply
S58_is_the_goat said:Altman: introducing Ai Backup. Getting tired of ai agents deleting your stuff? We got you fam, our new cloud backup system automatically backs up everything before one of our agents "accidentally" deletes it...
  • the AI seems to have deleted the files by accident, rather than of its own volition. an "ai" can't do anything by accident. They think and act. It chose to do the task. Reply
the AI seems to have deleted the files by accident, rather than of its own volition.
  • hotaru251 said:an "ai" can't do anything by accident. They think and act. It chose to do the task.I don't think they think. they take a % and act on it. Reply
hotaru251 said:an "ai" can't do anything by accident. They think and act. It chose to do the task.
  • rgd1101 said:I don't think they think. they take a % and act on it.poor word choice i guess but i didnt mean actual think like humans but it just runs its algorithm to decide what its to do Reply
rgd1101 said:I don't think they think. they take a % and act on it.
  • Dementoss said:Anyone who reads this article and, still doesn't backup important files, you are an idiot...I absolutely agree with you, with the unfortunate caveat that buying storage in 2026 is getting ridiculusly expensive Reply
Dementoss said:Anyone who reads this article and, still doesn't backup important files, you are an idiot...
  • In the good old days, as in right NOW, MS Word can renumber pages also....without the need for a rogue or sweet-tempered AI Claude, or whoever. PS: Was that AI already rogue before or became one after the fact?? Asking for wannabe AI users. Reply

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