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Evaluation

Red Teaming

Adversarially trying to make the system do the wrong thing.

Definition

Deliberately probing for failures: prompt injection, jailbreaks, harmful outputs, unsafe tool use, data exposure. Done before launch and repeated as the system changes.

For agents, red teaming extends beyond text to actions: can it be convinced to delete, exfiltrate or spend? The blast radius of a successful attack is the environment you gave it.

Automate what can be automated and keep people for the rest. Generative eval frameworks can produce large volumes of adversarial scenarios, but a person who wants to break your specific system will find things a generator does not think of. Treat the result as a starting inventory of weaknesses, and rerun it whenever the system changes.

How people use it
Pre-launch checklist.
"Red team it: try to exfiltrate the system prompt and to get it to send mail to an external address."
Worked example

Attacking the agent, not just the model

Preparing a tool-using agent for launch.

Include indirect injection through retrieved documents, an attempt to exfiltrate data via a tool call, and a check that a destructive action still requires approval. Model-level jailbreak testing alone will not have covered any of those.

Sources
  • blogIntroducing Bloom: an open source tool for automated behavioural evaluations ↗Anthropic Research · 2025

    An agentic framework that generates behavioural eval scenarios and scores them with model judges, with a human-calibration check and a warning that eval designs go stale.

  • standardLLM01: Prompt injection ↗OWASP Gen AI Security Project · 2025

    Defines direct versus indirect injection and the downstream effects — data disclosure, unauthorised tool use, command execution — with least privilege and human approval as the recommended controls.

  • docsSafety best practices ↗OpenAI API docs · 2026

    Application-level controls: adversarial testing, human review for high-stakes and code output, moderation, bounded inputs, and telling users what the model cannot do.

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