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.

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Read this episode online: https://newsletter.danielmiessler.com/p/ul-494

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➡ Prevent Risk At The Source with Cortex Cloud: https://www.paloaltonetworks.com/cortex/cloud/application-security

In this sponsored conversation, I speak with Sarit Tager, VP of Product Management at Palo Alto Networks, about how Prisma Cloud and their new ASPM solution are transforming cloud and application security by unifying data and deeply integrating business context into AppSec workflows.

We talk about:

Unifying AppSec, Cloud, and SOC into One Data Lake
How Palo Alto merged their products into a single system that consolidates runtime, code, identity, cloud, and SOC data, allowing for true context-aware risk prioritization and faster response times across the board.

From Detection to Dynamic Prevention
Why the future of application security isn’t just about discovering vulnerabilities, but enforcing smart, context-based guardrails during development, CI/CD, and build processes to prevent issues before they reach production.

AI-Powered Insight and the Future of Secure DevOps
How their system uses AI to analyze the full security posture, enrich findings, simulate attack paths, and recommend precise mitigations. The platform even helps guide security and engineering teams through better workflows, boosting velocity, and not blocking it.

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Chapters:

00:00 – Sarit’s Background and the Goal of Unifying Security Context
01:50 – Building a Single Data Lake for Cloud, SOC, and AppSec
04:28 – From Noise to Clarity: Fixing the Prioritization Problem in AppSec
06:47 – Using Business Context to Drive Risk-Based Decisions
10:18 – True App Ownership, Developer Velocity, and Aligning with Business Impact
13:12 – Continuous Discovery and Bringing External Signals Into One View
15:25 – Why App Grouping and Context-Rich Policies Increase Velocity
17:58 – How Attackers Are Already Building Their Own Unified Context (UEC)
20:45 – Prisma’s Control Points: IDE, PR, CI/CD, Image, Admission Control
21:56 – Bringing In Data From External Scanners and Enriching Coverage
24:23 – Ecosystem Signals, Query Language, and Intelligent Workflow Automation
25:05 – Closing Thoughts: Security and Developers Working Together

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