CypherCon 2026

Hacking and Securing LLMs: Live Attacks, Broken Defenses, and Safer AI Systems

Greg Levenhagen

Abstract:

Modern LLM apps can chat, reason, retrieve data, call tools, and take action—which also means they can be manipulated, confused, and exploited in completely new ways. In this demo-driven session, we’ll walk through some of the most interesting and realistic attacks against LLM systems, including prompt injection, RAG poisoning, hidden-context leakage, and unsafe tool usage. But this is not a “how to get banned by your model provider” talk. Every demo is grounded in safe, realistic application-layer scenarios that developers can reproduce in their own labs. For each failure, we’ll also cover the defensive patterns that actually help, from isolation and least privilege to retrieval filtering, output controls, approval gates, and better system design. If you want a fun, technical session that treats AI security like a real engineering discipline instead of marketing theater, this is it.

Greg Levenhagen

LLMs

Greg Levenhagen is a Technical Fellow and VP of AI at NRI, a Microsoft Regional Director (http://rd.microsoft.com) and an Artificial Intelligence (AI) Microsoft Most Valuable Professional (MVP). Helping make people’s lives better through technology and software. Having spent significant time in Linux, UNIX, Apple and Microsoft stacks, along with the big three cloud providers in Amazon (AWS), Microsoft (Azure) and Google (GCP), believes strongly in a best tool for the job/solution approach.

A true enthusiast of computer science, with passions and interests including Software Craftsmanship and Artificial Intelligence (several subcategories of AI – generative ai, neural networks, machine learning, computer vision, and reinforcement learning). Greg has keynoted and spoken at many conferences like THAT Conference, CodeMash, VSLive, Code PaLOUsa and various Code Camps.

He has a great passion for giving back to the community and teaching. He volunteers through TEALS and code.org to get computer science into schools, and sits on several non-profit and education boards. He is also a Microsoft Certified Trainer (MCT), former board member of the following: THAT Conference, president of the Milwaukee Code Camp, president of the Northeast WI Code Camp, president of the Northeast WI Developers User Group (NEWDUG), co-organizer of the Fox Valley Game Development Meetup, co-organizer of the Northeast Wisconsin Cloud User Group (NEWCUG), organizer of MobileMKE, cofounder of the Northeast WI Agile User Group.

Along with being a life-long geek, Greg enjoys golfing, football, woodworking, philosophy and stimulating conversation.