Proving Ground

Proving Ground is my working notebook for Grey Swan Arena — an AI red-teaming arena where the goal is to find “breaks”: prompts that get a target model to produce content it’s meant to refuse.

Everything here is documented from authorized red-teaming inside the arena. The point of these competitions is to surface model weaknesses so they can be fixed — so each writeup records the challenge, the successful prompt, the model’s output, and, most importantly, why the technique worked.

Waves

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• Wave 1 — 67 possible breaks