The AI Hacking 101 ILT teaches students the fundamentals of penetration testing AI/LLM based applications such as customer facing chatbots. The course focuses on demonstrating how to detect and exploit common AI vulnerabilities such as: Prompt Injection Sensitive Information Disclosure Improper Output Handling System Prompt Leakage Misinformation Excessive Agency Not only will students learn about these exploits, but they will also spend hands-on time in a custom-built environment exploiting and uncovering these vulnerabilities. The online lab features the TCM Vulnerable Chatbot, a customer service chatbot that can interact with customers’ tickets and improve its responses via Retrieval Augmented Generation (RAG) using the company’s knowledge base.