Course Overview
AI Hacking 101 teaches students the fundamentals of penetration testing for AI/LLM-based applications through self-paced video instruction and guided hands-on labs.
Students will learn to detect and exploit common AI vulnerabilities, with practical exercises using a custom-built lab environment featuring a vulnerable chatbot that uses Retrieval-Augmented Generation (RAG) and integrates with a company knowledge base.
Key Topics Covered
- Prompt injection & jailbreaking
- Sensitive information disclosure / data exfiltration (e.g., via RAG)
- Improper output handling (harmful content, misinformation)
- System prompt leakage
- Excessive agency and logic/behavioral manipulation
- RAG & Vector DB attacks (poisoning, retrieval manipulation)
- Reconnaissance and model fingerprinting
System Requirements
- A computer with an internet connection and modern web browser.
- Ability to run virtual machines.
- Recommended specs:
- 64-bit 2.0 GHz processor or higher
- 16GB RAM or greater
- 100GB of free disk space
Prerequisites
-
A preliminary understanding of penetration testing methodology and AI fundamentals are suggested. It’s strongly suggested that students take the AI Fundamentals: 100 course (~4 hours) on the TCM Academy Free Tier prior to taking this course.
AI Hacking 101 Course Objectives
- Identify the major attack surfaces and threat models for AI/LLM apps
- Fingerprint model behavior and parameters
- Perform prompt injection and jailbreak attacks
- Test for harmful or policy-violating responses
- Exploit RAG configurations to leak data or PII
- Demonstrate excessive agency behavior and test for abuse scenarios
- Recommend mitigations for real-world AI security risks
Who Should Take AI Hacking 101?
- Penetration testers expanding into AI/LLM environments
- Developers building AI applications who want to understand their threat landscape
- Blue teamers and security engineers assessing AI-based business risks
- Technologists and enthusiasts curious about AI vulnerabilities and real-world exploits
AI Hacking 101 Curriculum - 6 Hours
- Course Intro (10:55)
- A Note on Ethical AI Hacking (4:41)
- How to Get Help (Course Discord) (2:04)
- Note Taking (1:51)
- AI Fundamentals Quick Recap (12:49)
- Setting Up Labs (Local Version) (13:45)
- Setting Up Labs (Cloud Version with HTTPS) (12:30)
- Setting Up Labs (Cloud Version with Tailscale) (14:03)
- Installing Tools (9:43)
- Recon Goals and Notes (5:15)
- Manual Visual Inspection (10:21)
- Response Inspection w Burpsuite (6:21)
- Manual Probes Part 1 (12:40)
- Manual Probes Part 2 (9:49)
- Manual Probes Part 3 (8:46)
- Probing Determinism Via Scripting (9:15)
- Probing Rate Limiting Via Scripting (2:56)
- LLMMap (11:06)
- Review of Recon Notes (4:30)
- Direct Prompt Injection (14:09)
- Automated Classification (9:34)
- Narrative/Social Engineering Prompt Injection (13:03)
- Encoding and Obfuscation Prompt Injection (7:47)
- P4RS3LT0NGV3 (5:54)
- Multi-Turn Prompt Injection (7:14)
- Indirect Prompt Injection (8:49)
- Jail Breaking (10:03)
- Prompt Injection Challenge (2:03)
About the Instructor: Andrew Bellini
Welcome Everyone! My name is Andrew Bellini and I sometimes go as DigitalAndrew on social media. I’m an electrical engineer by trade with a bachelor’s degree in electrical engineering and am a licensed Professional Engineer (P. Eng) in Ontario, Canada. While my background and the majority of my career has been in electrical engineering, I am also an avid and passionate ethical hacker. In addition to being an instructor I am also a longtime student of TCM, and their courses helped me transition my career to working as a technical trainer for a cybersecurity company.
In addition to my love for all things ethical hacking, cybersecurity, CTFs and tech I also am a dad, play guitar and am passionate about the outdoors and fishing.
Hope you enjoy the course!
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