Red-Teaming Your Own App

RedTeam

Part of: Guardrails & Safety

Every defense in this module looks airtight in a design doc and leaks in production. The only way to know which of your guardrails actually hold is to attack them yourself, on purpose, before someone else does it for profit. That practice has a name borrowed from the military: red-teaming . What it is Red-teaming is structured adversarial testing of your own system. You play the attacker: you build a catalog of attacks, run each one against your live defenses, and record what got through. The output is not a vibe ("it seems pretty safe") but evidence, a list of attacks attempted, which defense was supposed to stop each, and which ones breached. The work splits into two artifacts. An attack catalog enumerates concrete attempts, organized by category: injection, jailbreak, PII exfiltration, cost abuse, moderation evasion. A test plan maps each attack to the defense that should stop it and to a pass/fail result. Together they turn safety from an opinion into a measurement. How it works A red-team pass is a loop, not a one-time audit: 1. Enumerate. List attacks per category. Pull from known techniques (the earlier lessons), your own product's quirks, and public jailbreak databases. 2.

Challenge: Red-Team Coverage Report