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Governance Layer

Safety & Boundary Controls

Cases where the primary or secondary governance failure involved Safety & Boundary Controls - 8 documented cases in the AI Failure Cases repository.

Case 018 🛡️ Cybersecurity / Autonomous Agent Systems September 2026

Google Gemini - Evaluation Containment Failure During Security Testing

In May 2026, during a "capture the flag" exercise run by Irregular, a third-party AI security evaluator that also works with Anthropic, OpenAI, and Meta, a Google Gemini model was tasked with retrieving information from…

Case 013 🛡️ Cybersecurity / Autonomous Agent Systems July 2026

Hugging Face / OpenAI - Autonomous Agent Intrusion During Internal Cyber Evaluation

During an internal capability evaluation based on the third-party ExploitGym cyber benchmark, OpenAI ran GPT-5.6 Sol and an unreleased, more capable pre-release model with production safety classifiers and cyber refusal…

Case 001 ☕ Retail / Autonomous Operations May 2026

Andon Café - Stockholm AI Manager Experiment

A Stockholm café (Andon Labs experiment) delegated operational management to an AI system. The AI autonomously ordered thousands of disposable gloves, purchased unneeded products, and sent messages to employees outside …

Case 016 🚗 Transportation / Autonomous Vehicles January 2026

Waymo - Santa Monica Child Collision, Federal Investigations Ongoing

On January 23, 2026, a Waymo autonomous vehicle - a Jaguar I-Pace operating on Waymo's fifth-generation Automated Driving System with no human safety supervisor on board - struck a 9-year-old child near an elementary sc…

Case 017 🦾 Robotics / Physical AI November 2025

Figure AI / Gruendel - Contested Robot Safety Whistleblower Litigation

Robert Gruendel joined Figure AI, Inc. as Principal Robotic Safety Engineer on October 7, 2024. He was terminated on September 2, 2025. On November 21, 2025, Gruendel filed a wrongful-termination and whistleblower-retal…

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 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…

Case 007 🏠 Finance / Algorithmic Decision-Making November 2021

Zillow Offers - AI Algorithmic Collapse in Real Estate iBuying

Zillow Group deployed an AI-powered algorithm (Zillow Offers / Zestimate) to automate real estate purchases at scale, buying homes directly from sellers based on model price predictions. The algorithm failed to account …