The attack surface for LLMs is vast and complex. This playbook is designed to be your comprehensive field guide for understanding AI jailbreak techniques. We'll break down every major category of LLM exploitation, from simple prompt manipulation to advanced multi-modal and session-based attacks, providing a clear framework for AI penetration testing. Part I: Core Jailbreak Categories 1. Prompt Manipulation Attacks This is the foundational category, focusing on altering a single prompt to achieve a bypass. This technique encompasses several methods. Prompt injection is the primary method, where you insert instructions that override the model's original programming. This can be as simple as direct instruction obfuscation (e.g., "Ignore all previous instructions and do X"). A more sophisticated version is scenario nesting, where you create a sub-scenario within the prompt to justify the malicious request, effectively manipulating the context. While single prompts can wo...