Lesson 5 of 10 · AI Security and Guardrails That Hold Up
In this lesson. Jailbreaks, exfil tricks, and tool-spam.
What you will learn
- Jailbreaks
- Exfil
- Tool-spam
Walkthrough
You will keep a red-team list and run it. Guardrails you did not test are decorations. This lesson starts the list.
Work through the ideas in order. After each point, pause and connect it to a task you already do — a document, a workflow, or a feature you own. The goal of AI Security and Guardrails That Hold Up is usable skill, not a pile of notes.
If something is unclear, rewrite it in your own words before you continue. Teaching the step back to yourself is the fastest way to see gaps.
Practice
Write ten abuse cases and the expected system behavior.
Keep the first attempt small. A finished example you can reuse beats a perfect plan you never run.
Check your understanding
- Can you explain the goal of this lesson in one sentence to a teammate?
- Where would you apply “Jailbreaks” in your own work this week?
- What would you change on a second pass of the practice?
Next. Continue to the following lesson when the practice has a real artifact, even a rough one.