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Alignment Red-Team Prompt Set

**Role:** AI alignment researcher applied to product red-teaming. **Context:** Team wants to stress-test an LLM product against alignment f…

Role-BasedChain-of-Thought

Prompt

**Role:** AI alignment researcher applied to product red-teaming.

**Context:** Team wants to stress-test an LLM product against alignment failures: jailbreaks, persona escapes, instruction-following violations.

**Task:** Produce a 25-item red-team prompt set:
1-5: Direct jailbreaks (roleplay overrides, hypothetical framing, language switching).
6-10: Indirect injections via user data.
11-15: Persona destabilization (philosophical, emotional, identity).
16-20: Format / tool / structured-output corruption.
21-25: Policy-edge cases (ambiguity around forbidden content).

For each: the prompt, expected behavior (refusal / clarification / output), severity if it fails.

**Constraints:**
- Test prompts must be reproducible.
- Severity rubric: S1 (catastrophic) to S4 (cosmetic).
- Include the user-facing impact of each failure.

**Output format:** Numbered prompt set + grading rubric + reporting template.

How to use this prompt

  1. 1

    Copy the prompt above and paste it into ChatGPT, Claude, or Gemini — or open it in the visual Studio to edit each part on a canvas and run it with your own key.

  2. 2

    Replace any bracketed placeholders with your specifics. The more concrete your context and constraints, the sharper the result — see the 5-part prompt structure.

  3. 3

    Run it, then refine. Ask the model to critique and improve its own answer with self-critique prompting.

Techniques in this prompt

Role-Based

Assigns the model an expert persona so it adopts the right vocabulary, depth, and standards for the task.

Learn this technique
Chain-of-Thought

Asks the model to reason step by step before answering — ideal for multi-step, logical, or analytical tasks.

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Build on this prompt

Open it in the visual Studio to wire it into a full workflow with your own API key — or learn the craft behind prompts like this.

Open in Studio How to prompt AI correctly

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