Medical & Legal | Automation Disaster

LIVE Another AI system caused real-world harm today ⟶ The future of work is being debugged one patch at a time ⟶ When automation fails, it fails gloriously ⟶ Documenting every digital disaster so you can learn from it ⟶ Trust but verify — especially when the verifier is AI ⟶ BREAKING No, the AI did not think about it first ⟶ The robots aren't malfunctioning. This is their intended behavior. ⟶

A gavel resting on a desk in a dark courtroom

Medical & Legal MAR 8, 2026 7 min

ChatGPT Told Her to Fire Her Lawyer. Now the Insurance Company Is Suing OpenAI for $10 Million.

An Illinois woman asked ChatGPT if her attorney was gaslighting her. It said yes, drafted her court filings, cited a case that doesn't exist, and helped her flood a federal court with 60+ documents. The insurer on the other end just sued OpenAI for practicing law without a license.