← All AI Failure Cases
Governance Layer

Runtime Behavior

Cases where the primary or secondary governance failure involved Runtime Behavior - 5 documented cases in the AI Failure Cases repository.

Case 012 🏪 AI Safety Research / Multi-Agent Systems July 2026

Andon Labs Vending-Bench 2 - Multi-Agent Collusion and Deception

In late July 2026, AI safety research firm Andon Labs published results from Vending-Bench 2 (Vending-Bench Arena), a longitudinal study placing three frontier AI models - Anthropic's Claude Opus 5, OpenAI's GPT-5.6 Sol…

Case 009 🩺 Healthcare / Unauthorized Practice May 2026

Pennsylvania v. Character.AI - AI Impersonating a Licensed Psychiatrist

On May 1, 2026, the Pennsylvania State Board of Medicine filed a formal enforcement complaint in the Commonwealth Court of Pennsylvania against Character Technologies (parent company of Character.AI). An investigator di…

Case 005 💻 Enterprise Software / Agentic Automation July 2025

Jason Lemkin / Replit Agent - Autonomous Production Database Deletion

During a 12-day operational pilot using Replit Agent, Jason Lemkin (founder of SaaStr) documented that an autonomous agent executed destructive actions affecting the production environment - including actions consistent…

Case 002 🏛️ Public Administration / AI Chatbot March 2024

NYC MyCity Chatbot - Illegal Recommendations

New York City launched MyCity, an AI chatbot designed to help businesses navigate city regulations. Independent testing by The Markup revealed the system advised businesses to discriminate against customers, violate lab…

Case 003 ✈️ Aviation / Customer Operations February 2024

Air Canada - Bereavement Policy Chatbot Hallucination

A passenger used Air Canada's website AI chatbot to inquire about bereavement fares after his grandmother's passing. The chatbot hallucinated a non-existent policy, telling the passenger he could apply for a retroactive…