AI Supply Chain in Practice: Generate Your First AI Bill of Materials | Oakley & Raidman | S2 E3
Security Mondays with Eva BennShow Notes
Hi, I'm Eva Benn. Every Monday morning I bring you some of the best global security leaders to talk through what's actually top of mind, the threats they're seeing, the tools they're using, and the decisions they're making right now. Every episode is designed to give you practical things you can go and implement in your organization this week. In March, attackers pushed two poisoned versions of Axios to npm and used it to drop a remote access trojan across Mac, Windows, and Linux. Microsoft tied it to a North Korean actor and CISA put out an alert. The LiteLLM package on PyPI got hit the same spring. By June, the Miasma campaign had compromised 32 Red Hat npm packages. When this happens, the question that decides your week is simple: do you know what you're running, and where? That's what a bill of materials answers, and it's why AIBOMs matter for the AI models and tools your teams are pulling down every day. In this episode, the two people leading the OWASP AI SBOM Initiative show how to build one and what to do with it. I'm doing my part by bringing you some of the best global leaders in the security industry every Monday, with practical tools and resources you can go use this week. This week, I sat down with Helen Oakley, who leads software and AI security at SAP and built the first open-source AIBOM Generator, and Dmitry Raidman, CTO and co-founder of Cybeats and one of the authors of the original SBOM standard. We talked about how to generate an AI Bill of Materials this week, how to read it, and where it fits with the new June 2026 executive order. What you'll walk away with: - A plain-English definition of an AIBOM and how it differs from a software SBOM - What the 2026 npm attacks (Axios, Miasma, LiteLLM) teach about the exposure question - How to generate your first AIBOM from a Hugging Face model, by website or CLI - How to wire AIBOM generation into CI/CD using CycloneDX output - One Monday-morning action on AI supply chain you can verify by Friday If you find this helpful, I'd appreciate a thumbs up, subscribe, and share. It helps more people find the show. Connect with Helen: LinkedIn: linkedin.com/in/helen-oakley Connect with Dmitry: LinkedIn: linkedin.com/in/draidman Tools and references: OWASP AIBOM Generator (try it): owasp-genai-aibom.org AIBOM Generator on GitHub: github.com/GenAI-Security-Project/aibom-generator OWASP AI SBOM Initiative: genai.owasp.org/ai-sbom-initiative White House executive order, June 2, 2026: whitehouse.gov/presidential-actions/2026/06/promoting-advanced-artificial-intelligence-innovation-and-security CISA alert on the Axios compromise: cisa.gov/news-events/alerts/2026/04/20 Microsoft: mitigating the Axios npm compromise Wiz: Miasma supply chain attack on Red Hat npm packages Chapters:00:00 — Why AI supply chain risk is growing so fast03:50 — The AI security concept every team needs to understand10:05 — Why AI makes supply chain attacks even harder12:11 — Where every AI supply chain program should start14:46 — How to generate your first AI Bill of Materials23:13 — The AI risks your AI BOM won't reveal30:12 — How to operationalize AI supply chain securityWant to hear from more voices in AI security? Security Mondays is a proud partner and supporter of the AI Cyber Magazine. Find it in any Lufthansa or Delta lounges. Not traveling soon? Get your copy here: https://aicybermagazine.comFollow along for more free cybersecurity education. 🤗LinkedIn: https://www.linkedin.com/in/evabenn/Instagram: https://www.instagram.com/evabennofficial/TikTok: https://www.tiktok.com/@evabennofficialWebsite: https://www.evabenn.com/
More from Security Mondays with Eva Benn
Remember the headlines about the 3 researchers at Hacktron AI who hacked OpenAI through a photo upload? After $3K in Claude tokens and less than 72 hours they had access to OpenAI’s internal code. Today, we’re hearing from Zayne Zhang, co-founder and CEO of Hacktron AI, and we’re going underneath the headlines into how they did it, how the economics of vulnerability exploitation have changed, and most importantly, what you can do about it.
If you have a hundred findings rated 9.2, which one do you fix first? The score can't tell you. Proof that an attacker can actually exploit it can.
In 2010, Dave DeWalt was CEO of McAfee when one bad update blue-screened computers across 1,672 companies in just 16 minutes. That was one bad update. Now imagine that same kind of accident in the age of autonomous AI agents, systems that can make decisions and take action across production environments at machine speed.
If you watch one video from Season 2 of Security Mondays, make it this one.10 episodes. Some of the most respected names in cybersecurity. Five themes that kept coming up again and again. I boiled it all down to under 15 minutes, so you can walk away with guidance you can use THIS week.Season 2 is officially a wrap. I got to sit down with leaders from completely different backgrounds, with completely different experiences. And they kept landing on the same five lessons. That's not a coincidence.A huge thank you to the incredible guests who made Season 2 possible:Rob Lee: AI security, cybersecurity fundamentals, and how AI is changing the speed of security.Thomas Rocha: AI threat intelligence and how the threats are changing.Helen Oakley & Dimitri Raidman: AI supply chain security and the risks hiding across the AI stack.Neil Provost: Security invariance, and building security that holds up as environments change.Joshua Copeland: Security theater, and why having a control is NOT the same as proving it works.Heath Adams: The attacker mindset, and thinking like the people trying to break your systems.Josh Bressers: The future of open source and the security challenges it faces.Tim Raines: AI aerospace strategy and the security implications of AI in critical environments.Rob Joyce: Offensive operations, national security, and lessons from decades in the field.Every conversation pointed to the same thing:AI is exposing every weak spot in the security playbook we already had, at a speed and scale we can no longer ignore.The five themes:1. AI changed the speed, not the fundamentals.2. Know what you have and what it can access.3. Assume agents will fail and contain the blast radius.4. Stop believing your security works. Test it.5. Finding vulnerabilities is getting cheap. Fixing them is the hard part.But HOW do you actually use any of this on Monday morning?Don't try to do everything at once. Pick ONE lesson. Put it into practice this week.That's how we roll here.Thank you for watching, commenting, and sharing these episodes with your teams. You made Season 2 what it was, and it has meant the world to me. ❤️Season 3 is coming soon, and we're kicking it off with Dave DeWalt on October 5th. Until then, I'll be here every Monday with practical AI security guidance you can turn into action.Which of the five themes hits closest to home for your team? Tell me in the comments 👇If you enjoyed this episode, I'd really appreciate a subscribe and a thumbs up.Follow along for more free cybersecurity education. 🤗---Want to hear from more voices in AI security? Security Mondays is a proud partner and supporter of the AI Cyber Magazine. Find it in any Lufthansa or Delta lounges. Not traveling soon? Get your copy here: https://aicybermagazine.comFollow along for more free cybersecurity education. 🤗LinkedIn: https://www.linkedin.com/in/evabenn/Instagram: https://www.instagram.com/evabennofficial/TikTok: https://www.tiktok.com/@evabennofficialWebsite: https://www.evabenn.com/
Hi, I'm Eva Benn. Every Monday morning I bring you some of the best global security leaders to talk through what's actually top of mind, the threats they're seeing, the tools they're using, and the decisions they're making right now. Every episode is designed to give you practical things you can go and implement in your organization this week.This week, I sat down with Rob Joyce, former Director of Cybersecurity at the National Security Agency and founder of Joyce Cyber. We talked about what changed once AI agents could run most of an attack on their own, and the concrete moves a security leader can make this week to keep pace. What you'll walk away with: - What still stops a top-tier attacker, and the one defense to add now. - What changed in AI-enabled offense, and the assumption to drop from your threat model. - How to check if you qualify for the NSA's free cyber services and sign up this week. - The identity audit to run today: phishing-resistant MFA and killing stale accounts. - The one thing to start Monday, and how to know by Friday that you moved. If you find this helpful, I'd appreciate a thumbs up, subscribe, and share. It helps more people find the show. Connect with Rob: LinkedIn: https://www.linkedin.com/in/rob-joyce-b43445116/ ResourcesUSENIX Enigma 2016 — "Disrupting Nation State Hackers" (talk): https://www.youtube.com/watch?v=bDJb8WOJYdA USENIX Enigma 2016 talk page + transcript: https://www.usenix.org/conference/enigma2016/conference-program/presentation/joyce NSA Cybersecurity Collaboration Center (free services, eligibility): https://www.nsa.gov/ccc Anthropic — "Disrupting the first reported AI-orchestrated cyber espionage campaign" (Nov 2025): https://www.anthropic.com/news/disrupting-AI-espionage Rob Joyce at the Secureframe National Cybersecurity Summit (six moves; AI offense): https://secureframe.com/blog/rob-joyce-dib-cybersecurity Rob Joyce testimony, House Select Committee on the CCP (Mar 5, 2025): https://docs.house.gov/meetings/ZS/ZS00/20250305/117983/HHRG-119-ZS00-Wstate-JoyceR-20250305.pdf XBOW tops HackerOne (2025): https://xbow.com/blog/xbow-on-hackerone-whats-next Chapters:00:00 — Why Hackers Don't Care Who You Are Anymore05:18 — AI Just Changed the Economics of Hacking07:55 — Why Every Organization Is Now a Potential Target10:15 — The Three Defenses You Can't Afford to Ignore17:04 — When AI Agents Become the New Insider Threat20:07 — Why Attackers Can Now Outpace Your Patch Cycle30:01 — The Cryptography Deadline Security Leaders Can't IgnoreWant to hear from more voices in AI security? Security Mondays is a proud partner and supporter of the AI Cyber Magazine. Find it in any Lufthansa or Delta lounges. Not traveling soon? Get your copy here: https://aicybermagazine.comAnd follow along for more free cybersecurity education. 🤗LinkedIn: https://www.linkedin.com/in/evabenn/Instagram: https://www.instagram.com/evabennofficial/TikTok: https://www.tiktok.com/@evabennofficialWebsite: https://www.evabenn.com/