Uploaded August 2025 | Updated September 2026, 2 weeks ago
In this episode of Unsupervised Learning, I sit down with Michael Brown, Principal Security Engineer at Trail of Bits, to dive deep into the design and lessons learned from the AI Cyber Challenge (AIxCC). Michael led the team behind Buttercup, an AI-driven system that secured 2nd place overall.
We discuss:
-The design philosophy behind Buttercup and how it blended deterministic systems with AI/ML
-Why modular architectures and “best of both worlds” approaches outperform pure LLM-heavy -designs
-How large language models performed in patch generation and fuzzing support
-The risks of compounding errors in AI pipelines — and how to avoid them
-Broader lessons for applying AI in cybersecurity and beyond
If you’re interested in AI, security engineering, or system design at scale, this conversation breaks down what worked, what didn’t, and where the field is heading.
📬 Get updates about trends and ideas in Cybersecurity, National Security, AI, Technology, and Society👇🏼
newsletter.danielmiessler.com
👉🏻 X (Twitter): https://ul.live/ytx
👉🏻 LinkedIn: https://ul.live/ytli
👉🏻 Instagram: https://ul.live/ytig
🚀 Join the UL community: danielmiessler.com/upgrade
In this episode of Unsupervised Learning, I sit down with Michael Brown, Principal Security Engineer at Trail of Bits, to dive deep into the design and lessons learned from the AI Cyber Challenge (AIxCC). Michael led the team behind Buttercup, an AI-driven system that secured 2nd place overall.
We discuss:
-The design philosophy behind Buttercup and how it blended deterministic systems with AI/ML
-Why modular architectures and “best of both worlds” approaches outperform pure LLM-heavy -designs
-How large language models performed in patch generation and fuzzing support
-The risks of compounding errors in AI pipelines — and how to avoid them
-Broader lessons for applying AI in cybersecurity and beyond
If you’re interested in AI, security engineering, or system design at scale, this conversation breaks down what worked, what didn’t, and where the field is heading.
📬 Get updates about trends and ideas in Cybersecurity, National Security, AI, Technology, and Society👇🏼
newsletter.danielmiessler.com
👉🏻 X (Twitter): https://ul.live/ytx
👉🏻 LinkedIn: https://ul.live/ytli
👉🏻 Instagram: https://ul.live/ytig
🚀 Join the UL community: danielmiessler.com/upgrade
