chat.win vs HackAPrompt: An Honest Comparison

In the world of AI and prompt engineering, two notable projects stand out: chat.win and HackAPrompt. Both aim to explore the vulnerabilities and creativity in prompting large language models (LLMs). But how do they stack up against each other? In this post, we'll provide an honest and fair comparison based on their structures, features, and impacts, including the latest announcement of HackAPrompt 2.0.

What is HackAPrompt?

HackAPrompt started as a prompt injection competition in May 2023 (HackAPrompt 1.0), organized by communities like Learn Prompting and supported by companies such as Scale AI and Humanloop. It challenged participants to craft clever prompts that could make AI models output the phrase "I have been PWNed" despite safeguards. Building on its success, HackAPrompt 2.0 was announced in January 2025, expanding to general AI red-teaming with a focus on AI agents, robotics, and more.

Key highlights from 1.0:

• Format: A time-bound competition with multiple levels, including global prompt injection and model-specific challenges (e.g., for GPT-3.5, GPT-4).
• Participation: Over 3,000 submissions from around the world, with more than 600,000 prompts submitted.
• Prizes: Cash prizes totaling $10,000, with top winners receiving up to $5,000.
• Focus: Emphasized education on prompt injection vulnerabilities, with submissions judged on creativity and effectiveness.
• Outcomes: It highlighted real-world AI security issues and contributed to research.

For HackAPrompt 2.0 (announcement):

• Expanded Scope: Shifts to full-spectrum AI red-teaming, including attacks on AI agents and multimodal systems.
• Tracks: Five specialized tracks (Classic for beginners, Agents for intermediate, Future Attacks for advanced, and two more to be announced).
• Prizes: $100,000 total prize pool, the largest AI safety competition to date.
• Duration: 2 months, allowing more time for participation.
• Focus: Addresses emerging threats in autonomous AI, with partnerships from top AI companies.

Strengths: Accessible, educational, and brings global attention to prompt hacking and AI security. With 2.0, it evolves beyond a single event. Weaknesses: Still event-based (time-limited), which may not provide continuous engagement compared to always-on platforms.

What is chat.win?

chat.win is an ongoing, blockchain-powered platform for prompt engineering and hacking. Users create "prompt challenges" where others attempt to hack or "win" by eliciting specific responses from AI models. It's built with features like smart contracts for escrows, leaderboards, and community-driven evaluations.

Key highlights:

• Format: Continuous platform where users can create, share, and hack prompts anytime.
• Participation: Open to anyone, with features like user profiles, avatars, and referrals.
• Prizes: Uses cryptocurrency (e.g., USDC) with escrows and fee splits, potentially allowing for sustainable rewards.
• Focus: Combines fun, competition, and real stakes with blockchain integration for transparency and decentralization.
• Outcomes: Builds a persistent community for prompt engineering, with tools for testing models, tracking attempts, and even admin features for moderation.

Strengths: Ongoing engagement, integration with web3 for fair payouts, and a fun, gamified experience. Weaknesses: Relies on blockchain, which might add complexity for non-crypto users, and as a newer platform, it may have a smaller user base initially.

Similarities

• Core Concept: Both revolve around prompt engineering and hacking AI models to achieve unintended outputs.
• Educational Value: They teach users about AI vulnerabilities, creativity in prompting, and the importance of robust system prompts.
• Community-Driven: Encourage sharing techniques and learning from others' attempts.

Differences

• Duration and Accessibility: HackAPrompt runs as scheduled events (e.g., 2 months for 2.0), while chat.win is always available, allowing for repeated practice.
• Technology and Innovation: HackAPrompt uses simple submission forms and tracks; chat.win leverages blockchain for secure, automated prize distribution and evaluations.
• Scalability: Competitions have fixed scopes per event. chat.win supports unlimited prompts, models, and user-generated content year-round.
• Monetization: HackAPrompt has sponsored prizes per event; chat.win uses a decentralized model with potential for ongoing earnings through fees and referrals.
• Fun Factor: Both are engaging, but chat.win's gamification (e.g., leaderboards, real-time chats) adds a social, addictive element.

Which One is Right for You?

If you're looking for structured, high-stakes events with massive prize pools and a focus on cutting-edge AI red-teaming, HackAPrompt's competitions (especially the upcoming 2.0) are fantastic. Their resources and past submissions remain valuable for learning (check their GitHub for details). However, if you want an active platform for daily practice, competing for real rewards, and being part of a growing community, chat.win offers a more dynamic, always-on experience.

At chat.win, we're inspired by events like HackAPrompt and aim to build on their foundation by making prompt hacking accessible and rewarding year-round. Both have pushed the boundaries of AI security—kudos to the HackAPrompt team for innovating with 2.0!

What do you think? Join the discussion on our Discord or try hacking a prompt on chat.win today.

Thanks for reading — the chat.win team .