What does red-teaming an LLM system involve?

Red-teaming means deliberately trying to make the system fail in harmful ways before real users do. I start by scoping it to the product. For an assistant with access to customer records and an email tool, the top risks are leaking one customer's data to another, sending messages nobody approved, and following instructions hidden in a retrieved document.

Then testers attack. Manual testing covers jailbreak styles, role-play framing, gradual multi-turn escalation and indirect prompt injection, such as a support ticket containing hidden instructions to export data. Because people cannot cover every variation, I add automated generation: a model produces many rephrasings and combinations, and classifiers or rules score which ones succeeded.

Findings are triaged by severity and how easy they are to trigger. Fixes are usually layered: tighter tool permissions and approvals, input and output filters, better system instructions and, where needed, model-level changes. Every successful attack becomes a regression test, and the suite runs before major releases, because new features and model upgrades can reopen old holes.