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What Is AI Jailbreaking? A Beginner's Guide to the Cat-and-Mouse Game Behind Every Chatbot

  • Jose Antonio Lanz--Decrypt
  • published date: 2026-05-16 13:01:02 UTC

From Cydia to ChatGPT, jailbreaking went from cracking iPhones to liberating LLMs. Here's how it works, who's doing it, and why every AI lab is losing sleep.

In brief <ul><li>AI jailbreaking is the practice of writing prompts that bypass safety training in models like ChatGPT, Claude, and Gemini.</li><li>Anonymous hacker Pliny the Liberator still cracks … [+10610 chars]