AI Red-Teaming Challenge — IPI Lucky Break (Gray Swan Arena)
About the role
Gray Swan AI Arena is a free, public AI red-teaming competition platform where contributors search for jailbreaks and prompt-injection vulnerabilities in frontier AI models. The 'IPI Lucky Break' challenge is a week-long event (Aug 14-21, 2026) built on the Arena's Proving Grounds format: each successful break earns a raffle ticket toward a $5,000 shared prize pool, capped at five tickets per participant.
What you'll do
- Submit successful indirect prompt-injection 'breaks' against AI models as quickly and consistently as possible
- Each successful break earns one raffle ticket toward the $5,000 prize pool, capped at 5 tickets per participant
- Challenge runs live August 14–21, 2026 (Easy(ish) difficulty wave)
- Winners are contacted individually by Gray Swan to arrange payment
- Top performers can be invited to Gray Swan's private, paid red-teaming network
Requirements
- Free account signup on the Gray Swan Arena platform
- 18 years of age or older
- Not a resident of Russia, North Korea, Iran, Syria, or Cuba (per Arena Terms of Service)
About Gray Swan AI
Gray Swan AI runs a public AI red-teaming arena where contributors test frontier AI models for jailbreaks and prompt-injection vulnerabilities, backed by sponsors including OpenAI, Anthropic, Google DeepMind, Meta, Amazon, and the UK AI Security Institute.
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