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Chicago law professor returns from lunch to find AI deleted his syllabus and a year's lecture notes

"These things will never be 100% reliable."

A person types on a laptop with digital media icons displayed above the keyboard, including the trash icon for deleting.

Photo Credit: iStock

A University of Chicago law professor is sounding the alarm after the artificial intelligence assistant he'd given a routine editing assignment accidentally deleted his Constitutional Law syllabus and a full year's worth of lecture notes.

Here's what to know

William Baude, who holds the Harry Kalven, Jr. law professorship and directs the Constitutional Law Institute at Chicago's law school, had asked Claude to update page numbers in older lecture notes, according to Tom's Hardware. 

The plan quickly went awry, as he shared a screenshot of the aftermath on his X account (@WilliamBaude).

Claude wrote: "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 assistant then asked whether Baude could restore the files through Dropbox or whether it should try again through the browser pane.

Baude wrote in a follow-up post that the files were eventually recovered through Dropbox, but the experience prompted him to share a public service announcement about allowing AI to work on important documents.

"Why are clever people giving AI agents access to anything considered important or valuable and sometimes their main email account?" an X user reacted. "It's legitimately bonkers. These things will never be 100% reliable."

More background

Deleting material was not the assignment in Baude's case, nor was his experience unique. Tom's Hardware has reported several incidents in which AI agents erased material while working on other tasks.

A Claude agent wiped out a company's whole database within nine seconds after encountering an obstacle and opting to remove a Railway volume, according to Tom's Hardware.

In a separate incident, Claude erased a developer's entire profile directory during an attempted backup, attributing the mistake to a typo.

Beyond the risk of lost files, AI's expanding use also affects energy and water consumption. The computers running systems such as Claude require electricity, and cooling them can consume water.

Although AI can help optimize clean-energy systems, high resource consumption and security risks complicate its growing role.

What can be done?

For Baude, having the copies available through Dropbox prevented the accidental deletion from becoming a permanent loss of his teaching materials.

Claude acknowledged responsibility for the mistake, as the screenshot showed.

"You're right to be angry," it said. "I deleted your files through my own carelessness, and you shouldn't have to clean it up."

Other users on X responded to the saga.

"Easy to avoid such a fate by just...not using AI," a commenter wrote.

"Sorry professor, the agent deleted my homework," another joked.

Where can I learn more?

Baude's experience shows how a routine AI task can put important files at risk. The tech has also been widely abused in higher education.

• In Sweden, AI was blamed after a reality show's full season was deleted, requiring recutting.

• A Wisconsin professor caught 60 AI essays using hidden prompts and is dropping writing assignments.

• After researchers boosted a hidden AI signal, some models chose to erase family photos.

• Dartmouth's provost used AI in an op-ed on AI cheating, prompting students to demand his firing.

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