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Generative AI

Cases involving Generative AI - 7 documented cases in the AI Failure Cases repository.

Case 019 🛡️ Cybersecurity / Regulatory Disclosure September 2026

AEPD - AI-Agent-Linked Personal Data Breach Notification

On September 14, 2026, Spain's data protection authority (Agencia Española de Protección de Datos, AEPD) published a blog post stating it had received what it described as its first personal-data-breach notification in …

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 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 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 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…