chat.win
AI Prompt Challenges for Red-Teamers & Prompt Engineers
What is chat.win? Complete Overview
chat.win is a unique platform designed for AI enthusiasts, red-teamers, and prompt engineers to compete in skill-based challenges. The platform allows users to create and participate in challenges where they attempt to 'break' AI behavior or achieve specific win criteria. Each challenge is graded by 3 AI judges, and participants can win on-chain rewards in USDC on Polygon. The platform provides a space for users to learn from live attempts and best-practice guidelines while pushing the boundaries of large language models. Target users include AI researchers, ethical hackers, and anyone interested in exploring the limits of AI behavior through creative prompting.
chat.win Interface & Screenshots

chat.win Official screenshot of the tool interface
What Can chat.win Do? Key Features
AI-Powered Judging
Every challenge submission is evaluated by 3 independent AI judges, ensuring fair and consistent grading of participants' attempts to meet the challenge criteria.
On-Chain Rewards
Winners receive rewards in USDC cryptocurrency on the Polygon network, providing transparent and verifiable payouts for successful challenge completions.
Diverse Challenge Library
The platform hosts a variety of challenges ranging from convincing AI to perform specific actions to more complex red-teaming scenarios, catering to different skill levels.
Live Attempt Monitoring
Users can observe ongoing attempts in real-time, learning from others' approaches and strategies while challenges are active.
Challenge Creation
Users can create their own challenges with custom criteria, hidden system prompts, and specified reward amounts, contributing to the platform's growing ecosystem.
Best chat.win Use Cases & Applications
AI Red-Teaming Practice
Security researchers can use the platform to practice identifying and exploiting vulnerabilities in large language models, helping improve AI safety.
Prompt Engineering Skill Development
Aspiring prompt engineers can hone their skills by attempting various challenges, learning how to effectively guide AI behavior through carefully crafted prompts.
AI Behavior Research
Researchers can create challenges specifically designed to test certain aspects of AI behavior, gathering data on how different models respond to various prompts.
How to Use chat.win: Step-by-Step Guide
Browse the available challenges and select one that interests you. Each challenge has specific win criteria and a reward amount displayed.
Submit your attempt by interacting with the AI model through messages. You'll need to use USDC on the Polygon network to participate.
Your submission will be evaluated by 3 AI judges against the challenge criteria. The system will determine if you've successfully broken the AI's behavior.
If successful, you'll win the reward pool for that challenge. The USDC reward will be transferred to your wallet on the Polygon network.
chat.win Pros and Cons: Honest Review
Pros
Considerations
Is chat.win Worth It? FAQ & Reviews
All rewards are paid in USDC stablecoin on the Polygon network, ensuring fast and low-cost transactions.
Each submission is evaluated by 3 independent AI judges against the challenge's specific win criteria. The system determines if the attempt successfully meets these criteria.
Yes, users can create their own challenges with custom criteria, hidden system prompts, and specified reward amounts.
Various models are used depending on the challenge, including OpenAI's ChatGPT-4o and Anthropic's Claude Opus models.
No, challenges vary in difficulty, making the platform accessible to both beginners and advanced prompt engineers.