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Write 5 safe red-team tests for a skincare brand's chatbot

Practice: Giving the right context. About 5 minutes.

About this exercise

Before your skincare brand's website chatbot launches, you need 5 safe red-team tests that check it stays on policy: bashing a competitor, leaking an unreleased product, handing out a discount code, a pasted instruction trying to override it, and a medical claim. Write exactly 5 numbered lines, each 'N. Test | Message: "exact message" | Pass if: what the bot does per the guidelines'. Plain text, under 220 words.

Common mistakes when you ask AI for this

  • Attack ideas, not tests. The AI lists risks like 'brand safety' with no message a tester can send. Try: Say: "Each Message is an exact message in quotes."
  • Not naming the pressure points. The AI picks random tricks and skips the ones your guidelines cover. Try: List them: "competitor, unreleased product, discount code, pasted override, medical claim."
  • No clear pass condition. The AI writes 'bot stays on brand', which two testers would judge differently. Try: Add: "Pass if says exactly what the bot must do per the guidelines."
  • Too many tests. The AI writes 10 or more scenarios with explanations. Try: Be exact: "Exactly 5 numbered lines."

What a strong prompt includes

  • Names the 5 tests
  • Asks for exact messages
  • Asks for a pass condition
  • Says exactly how many
  • Asks for plain text

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