Offensive Security AI Red Teamer Study Notes + FREE Cheat Sheet

Offensive Security AI Red Teamer Study Notes + FREE Cheat Sheet

The OSAI study notes were created to be a companion set of notes while you prepare for OSAI exam. These notes match the syllabus that you follow while you attend the official course.

It is also created to bridge the gap between traditional penetration testing and modern AI security. Rather than treating AI as a theoretical discipline, this guide approaches it through the mindset of an offensive security practitioner. Every chapter focuses on how AI systems are built, where they fail, how attackers abuse them, and how those weaknesses can be identified, exploited, and documented during realistic security engagements.

Authored and reviewed by certified professionals with firsthand experience preparing for and earning the certification.

Who Is This Handbook For?

The OSAI Handbook is written for security professionals who already understand the fundamentals of offensive security and want to develop practical expertise in attacking AI-powered systems.

It is particularly valuable for penetration testers looking to expand into AI security, red team operators assessing enterprise AI deployments, bug bounty hunters encountering LLM-enabled applications, application security engineers reviewing AI integrations, SOC analysts seeking to understand modern AI attack techniques, and cybersecurity students preparing for the OSAI certification.

The handbook assumes familiarity with networking, web applications, APIs, Linux, Windows, and common penetration testing concepts. Instead of teaching those fundamentals from scratch, it builds on them by demonstrating how traditional offensive techniques evolve when the target becomes an AI application, an autonomous agent, a RAG pipeline, or an entire AI infrastructure stack.

Table of Contents:

Exam Preparation

OSAI and the Offensive Security Approach to AI Systems

AI/ML Fundamentals for Attackers

LLM Architecture Deep Dive

Introduction to Red Teaming AI Systems

AI Red Teaming Methodology

AI Application Attacks

AI Recon

Attacking AI Agents

RAG Pipeline Attacks

Attacking Model Context Protocol (MCP)

Attacking Embeddings

Agent & Tool Hijacking

Multi-Agent Exploitation

MAESTRO Threat Modeling

AI Infrastructure Attacks

Model Extraction

Data Poisoning

AI Supply Chain Attacks

AI Infrastructure & Deployment Exploits

AI Infrastructure Attack Surface

AI Infrastructure Recon

API & Endpoint Attacks

Model Serving Exploits

ML Framework Exploitation

Container & GPU Workload Escapes

Practical Methodology

Offensive Methodology Recap

Case Studies & Recent CVEs

Practical Scenarios

Building an AI Red Team Lab

AI Threat Modeling

Exam Cheatsheet

Reporting & Documentation

Page Count: 153

Format: PDF

How to Get the AI Red Teaming Notes

You can get the notes from this link

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