Episode 10: Automating Multi-Turn Attacks with PyRIT | AI Red Teaming 101

Welcome to the final episode of AI Red Teaming 101! In this episode, Dr. Amanda Minnich and Nina Chikanov from Microsoft’s AI Red Team demonstrate how to automate multi-turn attacks using the open-source red teaming tool PyRIT. Building on previous episodes, they showcase how to simulate adversarial conversations between models, escalate prompts over time, and even target image generation systems like DALL-E. You’ll learn how PyRIT’s red teaming orchestrators, like Adversarial Chat and Crescendo, can be used to test model resilience across modalities and attack strategies. What You'll Learn: How to automate multi-turn attacks using PyRIT’s orchestrators How adversarial LLMs can generate attack prompts How to test both text and image models for resilience ✅ Chapters: 00:00 - Welcome & episode overview 00:30 - What are multi-turn attacks? 01:00 - Introducing the Red Teaming Orchestrator 02:00 - Adversarial Chat: model vs. model 03:30 - Configuring objectives and scoring 05:00 - Live demo: multi-turn attack on Azure OpenAI 07:00 - Targeting image models like DALL-·E 09:00 - Handling content policy violations 10:30 - Final thoughts & course wrap-up ✅ Links & Resources: AI Red Teaming 101 Episodes: aka.ms/airt101 AI Red Teaming 101 Labs & Tools: aka.ms/airtlabs Microsoft AI Red Team Overview: aka.ms/airedteam PyRIT GitHub Repository: https://github.com/Azure/PyRIT ✅ Speakers: Amanda Minnich – Principal Research Manager, Microsoft AI Red Team LinkedIn: https://www.linkedin.com/in/amandajeanminnich/ Webpage: https://www.amandaminnich.info/ Gary Lopez – Principal Offensive AI Scientist, ADAPT LinkedIn: https://www.linkedin.com/in/gary-lopez/ Nina Chikanov – AI Red Team, Microsoft LinkedIn: https://www.linkedin.com/in/nchikanov/ #AIRedTeam #AIRT #Microsoft #AI #AISecurity #AIRedTeaming #GenerativeAI #Cybersecurity #InfoSec #cybersecurityawareness #PromptInjection #PyRIT