AI Engineer World’s Fair regular bird tix will sell out ~today! Join us next week ahead of the Late Bird price hike and get >$40,000 in sponsor credits for attending! Thanks to the US Government issuing an export control directive on Mythos and Fable, the risks of jailbreaks and (industry term) indirect prompt injection are suddenly the talk of the town, though we have been covering AI security for a few years now, from Hackaprompt to the enigmatic Pliny the Elder. Zico Kolter, member of OpenAI’s board of directors on the Safety & Security Committee, and Matt Fredrikson, CMU professor and CEO of Gray Swan, co-authored the definitive paper on Indirect Prompt Injections, and Gray Swan were cited authorities on the Mythos model card, directly investigating the exact capabilities that are under scrutiny right now: We seized the opportunity to ask them the state of AI Red Teaming, and Shade, the adversarial red teaming tool that Anthropic used to evaluate the robustness of their models against prompt injection attacks in coding environments. Shade is part of their overall toolkit covering Simon Willison’s Lethal Trifecta, including Cygnal, an AI guardrails product, and the world’s largest AI Red Teaming Arena, including AIRT celebrity Wyatt Walls. All of this security tooling, and yet, we’re only staving off the inevitable. The risks of extremely smart AI increasingly feel like gray swan events: an event that everyone can see coming. In this episode, Gray Swan cofounders Zico Kolter and Matt Fredrikson join swyx to explain why AI security is not just “cybersecurity with AI,” why agents introduce a new class of vulnerabilities, and why the next major AI incident may be a gray swan: unlikely, but clearly visible before it happens. We go deep on prompt injection, automated red teaming, model robustness, agent identity, computer-use agents, enterprise guardrails, and the emerging AI insurance/compliance stack. Zico and Matt also explain why frontier models are not automatically safer as they scale, why specialized red-teaming models can now beat humans at breaking AI systems, and why the future of AI security may depend on AI systems attacking, defending, and interpreting other AI systems. We discuss: * Why AI systems need a different security mindset from traditional software * How prompt injection creates a new exploit class for agents like Codex and Claude Code * Gray Swan Arena and the rise of community red teaming * Shade: AI that can outperform humans at breaking models * Why LLMs are an alien form of intelligence that fail differently from humans * Human vs browser-agent robustness and why humans ranked fourth * Why eval awareness and capability elicitation matter * Cygnal: Gray Swan’s guardrail model for policy enforcement * Why bigger models do not automatically become more robust * The lethal trifecta: untrusted data, private data, and exfiltration * Why “just prompt it better” is not enough for enterprise AI security * OpenClaw, computer-use agents, and the agent security nightmare * Agent-native identity, permissions, and enterprise deployment * Why AI security may become part of insurance and compliance * Why the first major AI prompt-injection breach may be inevitable Gray Swan * Website: https://www.grayswan.ai/ Zico Kolter * X: https://x.com/zicokolter * Website: https://zicokolter.com/ * LinkedIn: https://www.linkedin.com/in/zico-kolter-560382a4/ Matt Fredrikson * Website: https://www.mattfredrikson.com/ * LinkedIn: https://www.linkedin.com/in/matt-fredrikson-7596349/ Timestamps 00:00:00 Introduction 00:02:31 Why AI Security Is Different 00:06:38 Testing Claude, Codex, and Prompt Injection 00:07:47 Gray Swan Arena and Automated Red Teaming 00:11:14 AI That Breaks Models Better Than Humans 00:14:00 LLMs as Alien Intelligence 00:19:00 Humans vs AI Agents 00:24:35 Red Teaming, Jailbreaks, and Capability Elicitation 00:26:11 Cygnal: Guardrails for AI Agents 00:34:04 The Lethal Trifecta 00:39:31 Can AI Automate AI Research? 00:45:47 OpenClaw and the Computer-Use Security Problem 00:50:44 Agent Identity, Permissions, and Enterprise AI 00:54:24 The Future of AI Security 01:00:30 AI Insurance and Compliance 01:04:32 The Gray Swan Event Everyone Sees Coming 01:06:04 Closing Thoughts Transcript Introduction: Gray Swan, AI Security, and CMU Swyx [00:00:00]: We’re here in the studio with Gray Swan, Matt and Zico. Welcome. Zico [00:00:08]: Great to be here. Matt [00:00:09]: Thanks for having us. Swyx [00:00:10]: You’re visiting from Pittsburgh? The home of all good computer science. I don’t know if I’m overstating things. A very strong university. Zico [00:00:18]: CMU has been the center of a lot of AI since really the dawn of the field. Swyx [00:00:22]: Especially a lot of self-driving and some language learning. Congrats on your Series A. You’re here because you’re attending Snowflake Summit, and Snowflake is one of your investors. Let’s introduce crisply at the top: what is Gray Swan, and what have you chosen as your startup domain? Matt [00:00:42]: At Gray Swan, our mission is to empower everyone to use AI safely and securely. Large language models are software, and if you want to deploy them or build applications on top of them, you need to understand the vulnerabilities and what can go wrong. That includes everyday mistakes, like an agent making the wrong tool call, but also worst-case scenarios where an attacker has an incentive to make your agent misbehave, leak data, or steal credentials. Gray Swan grew out of our research at Carnegie Mellon, where Zico and I have spent over a decade studying new vulnerabilities and attack surfaces in deep learning systems: how to test for them, understand their severity, and make inference more robust. Adversarial Examples and Why AI Security Is Different Swyx [00:02:05]: Honestly, a very fruitful area of study for any academic. Throwback, this is 10 years ago, which is basically the entirety of me. I got a lot of inspiration from Ian Goodfellow, a friend of the pod, and this is one of those initial adversarial settings. Matt [00:02:23]: This paper was directly inspired by Ian’s work. Swyx [00:02:29]: Zico, what about your side of the story? Zico [00:02:31]: Like Matt, I have been faculty at Carnegie Mellon for a while. Fundamentally, we believe in the transformative power of AI. It has already transformed the software ecosystem, and it will transform many other ecosystems going forward. The issue is that these systems behave very differently from the software we are used to. I do not just mean that AI can find vulnerabilities in software, though it can. I mean that AI systems have inherent vulnerabilities of their own. They can be tricked in ways people can be tricked, so you need a different security mindset. Zico [00:03:23]: This matters especially when there is the possibility of correlated failures. It is not just that there are many AI systems out there; it is that everyone is using a few models. If you find vulnerabilities in agents that everyone uses, like Codex and Claude Code, you have a new class of exploit. The labs are doing a lot of work here, but when a new platform emerges, a separate security system often emerges alongside it. That is where we are with AI: there is a need for specifically minded AI safety and security providers, and the demand is only going to grow. Treating Models as Untrusted Systems Swyx [00:04:55]: I want to highlight right at the top that this is not a cyber episode in the traditional sense. A lot of people looking at the title might think that, but you’re actually trying to treat these models inherently as untrusted entities? Zico [00:05:11]: Exactly. This is a common conflation because AI is also good at cybersecurity problems, both solving them and causing them. But AI systems themselves introduce new vulnerabilities. Gray Swan is not about using AI to make your cyber infrastructure better; it is about understanding and mitigating the security risks you bring in when you adopt and deploy AI. Matt [00:05:49]: A big part of that is how people are using artificial intelligence. Once you build entire autonomous systems on top of models and integrate them into your larger platform or network, you have a potential cybersecurity risk. The goal is to mitigate the risk posed by the AI as it relates to your broader cybersecurity goals. Testing Claude, Codex, and Indirect Prompt Injection Zico [00:06:17]: Part of this is red teaming. One reason we reached out to you was that you were involved in the Claude Mythos preview, where you were one of the authorities on IPI, or indirect prompt injection. When you receive a model, it does not have to be Mythos, but that is the most prominent one right now: what do you do with it? Matt [00:06:38]: We do a range of things. In the Mythos case, the concern from Anthropic was how robust the model is to indirect prompt injection. If you operate a coding agent and use Mythos as the model, it will fetch untrusted content and read text you do not control. How robust will it be at staying true to its original objective and not getting hijacked? We also help frontier labs test their safeguards for issues like cyber misuse. Broadly, we provide adversarial safety and security evaluations so model builders can assess progress from one iteration to the next. Zico [00:07:37]: They also do this in-house, and Anthropic is very ideologically inclined to do it. What do they choose to outsource versus keep in-house? Gray Swan Arena and Automated Red Teaming Matt [00:07:47]: So there are two things that I think, we stand out for. One is the Gray Swan Arena. So we operate a community of red teamers. We provide, prize challenges. a lot of these come from the needs of the lab sponsors. so to an extent gamify red teaming objectives, put up a prize pool, and pay people when they find ways to circumvent and violate whatever the safety and security objectives of the model developers wer
