Guardrails beyond Vibes

Jeffrey Zhang, Security Engineer, Stripe & Siddh Shah, Software Engineer, Stripe, speak at [un]prompted 2026 on: Guardrails beyond Vibes: Shipping Security Agents in Production. In this talk, we’ll share how Stripe is using AI agents to streamline t...

Jeffrey Zhang, Security Engineer, Stripe & Siddh Shah, Software Engineer, Stripe, speak at [un]prompted 2026 on: Guardrails beyond Vibes: Shipping Security Agents in Production.

In this talk, we’ll share how Stripe is using AI agents to streamline two high-friction security workflows: threat modeling and security request routing. We’ll cover the practical design choices that made these agents reliable in practice - modular orchestrator/child architectures, targeted tools, structured inputs/outputs, and validation to reduce variance and improve determinism. We’ll also walk through how we measure and improve agent quality over time using offline and online evaluation loops, including how we handle subjective outputs in threat modeling versus higher-signal feedback in routing. The session closes with concrete lessons on what worked, what didn’t, with automating security workflows without losing user trust.