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Professor loses syllabus after asking Claude to renumber pages

A University of Chicago law professor saw an entire Constitutional Law syllabus disappear after asking Claude to renumber pages, according to a daily AI digest.

By GennnAi··1 min read

According to the Daily AI Caffeine newsletter of November 14, the full syllabus and a year of lecture notes were gone. Dropbox was then able to recover everything. The incident involves Claude, Anthropic's assistant, used for a formatting operation on documents. The summary reviewed does not detail the technical circumstances of the deletion or the version of Claude used. No further consequences are reported.

Source: Daily AI Caffeine, published on November 14, 2026.