AI Security After Codex and Claude Code — Zico Kolter & Matt Fredrikson, Gray Swan
About this episode
From the show’s notesAI agents are becoming powerful enough to write code, browse the web, access private data, and act on our behalf — but the security model for this new world is still being invented. 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.
Read the show’s notes in full
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
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Gray Swan
• Website: grayswan.ai
Zico Kolter
• X: x.com/zicokolter
• Website: zicokolter.com
• LinkedIn:
