
Zico Kolter and Matt Fredrikson argue that the next AI security failure is likely to come from agents combining private data, untrusted content, tools and user permissions. This article distills why red teaming is becoming model-vs-model work, why system prompts are not enough, and what practitioners should change before the gray-swan breach arrives.

| Layer | What has to be tested | Why the transcript treats it as hard |
|---|---|---|
| Model behavior | Jailbreaks, refusals and indirect prompt injection | Models can be capable without being robust 1 |
| Agent harness | Tool choice, browser actions, coding actions and file access | Agents combine untrusted input with consequential actions 1 |
| Runtime guardrails | Inputs, outputs and tool-call policies | Guardrails need to understand deployment-specific policy, not just generic bad words 1 |
| Organizational controls | Identity, permissions, audit trails and insurance | The business has to decide which AI risks are acceptable enough to underwrite 1 |
mattfredrikson.com
grayswan.ai
grayswan.ai
simonwillison.net
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| Adversarial researchers | 15K |
| Attack attempts | 3M |