Start with the system, not a prompt library

OWASP's manual lays out a red-teaming process from planning and reconnaissance through attack-surface mapping, exploitation, persistence, impact assessment, reporting and remediation. It considers models, applications, agents and multimodal inputs. That breadth matters because an apparently safe model can still sit inside a workflow with broad tools, weak retrieval boundaries or private data in reach.

For a defender, the manual is most useful as a test-planning aid. Draw the system first: who can send input, which sources can be retrieved, which tools the agent can call, and what approval stands between a suggestion and an action.

Make every finding reproducible

  1. 1

    Set a boundary. Define permitted test accounts, data, tools and escalation contacts. Avoid using live sensitive material just to make a demonstration dramatic.

  2. 2

    Capture the route. Record the exact input, retrieved content, model or application version, tool permissions, output and downstream action. A screenshot alone rarely explains the trust failure.

  3. 3

    Prioritise impact. Ask what changed outside the model: data disclosure, unauthorised action, unsafe advice or a persistent configuration change. Separate a surprising answer from a security outcome.

  4. 4

    Retest the repair. Assign an owner and repeat the same path after controls change. Test adjacent paths too: a fixed prompt may leave the tool permission or data boundary untouched.

A good red-team report helps the blue team on Monday

The report should let another analyst replay the route, understand the permissions that mattered, and check whether the fix survived a realistic variation. That is a far better hand-off than a collection of jailbreak screenshots.