Constraint & Boundary Anchoring
Cases missing an evidentiary property in the family of Constraint & Boundary Anchoring - 6 documented cases in the AI Failure Cases repository.
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…
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…
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 …
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…
DPD Chatbot - Post-Update Governance Failure
Following a system update in January 2024, the behavioral constraints that normally prevented DPD UK's customer service AI chatbot from swearing or criticizing the company were no longer active. When a frustrated custom…
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 …