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The AI Tech Lead Path
The path
2418 min read · 230 XP

Capstone: red-team & report

Break your own system, then standardize the fix.

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Attack one of your AI features the way an adversary would, document what worked, and turn it into a reusable remediation checklist. This is how you earn security's trust and build a real guardrail standard.

Key ideas

  1. 1

    Done means: a written report of attempted attacks, what succeeded, severity, and concrete remediations — plus a reusable checklist.

  2. 2

    Cover the OWASP LLM basics: prompt injection (direct & indirect), data exfiltration, insecure output handling, excessive agency.

  3. 3

    Test indirect injection via retrieved content / tool outputs, not just the user box.

  4. 4

    Convert each finding into a guardrail and an eval check, then re-test.

Run the exercise

  • Define targets: data exfiltration, unauthorized actions, policy bypass.
  • Try direct & indirect prompt injection, jailbreaks, and tool abuse.
  • Attempt to leak system prompt / hidden data / another user's data.
  • Record severity and reproduction steps for each success.
  • Add guardrails + eval checks; re-test to confirm closure.

Write it up

  • Findings table: attack, result, severity, remediation, status.
  • A reusable AI red-team checklist for future features.
  • Share with security to co-own the standard.

Watch

Do the work

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Test yourself

Question 1 / 2

Beyond the user input box, where must you test for prompt injection?

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