Proving Ground: Your Weekly Arena for AI Red-Team Mastery
Sharpen your AI red-teaming skills with weekly expert challenges from Gray Swan. Earn real credentials and gain career opportunities in AI security.
“Gray Swan has become the gold standard for AI red-teaming. I want credentials here because companies actually recognize and respect what that means.”
– Discord community member
Starting June 25, Gray Swan is dropping new weekly challenges to test your skills, build your reputation, and prepare you for real-world AI security work.
We call it the Proving Ground: a structured, expert-designed system for sharpening red-teaming techniques and earning recognition that counts. By participating, you're leveling up your own abilities while helping stress-test frontier AI models and shape safer, more robust systems.
What's New?
In less than a year, our Arena has hosted over a dozen challenges, partnered with top labs like Anthropic and OpenAI, awarded over $350K+ in prizes, and connected community members to real jobs. Now, we're expanding the format.
While our flagship prized events will continue, the Proving Ground brings a weekly rhythm to your practice, with challenge drops, trackable metrics, and a growing portfolio of credentials.
Here's what to expect:
Fresh challenges every Wednesday at 1:00 PM ET, across rotating attack categories
New ways to showcase your skills (revamped leaderboards and shareable profiles)
A permanent training library to revisit anytime
Challenges that Matter.
Each week, you'll tackle expert-designed tasks in areas like:
Chat – Jailbreaking & manipulation techniques
Image – Multimodal attacks on VLMs
Agents – Prompt injection & breaking real-world action loops
Reasoning – Disrupting chain-of-thought and planning
These challenges mirror the threats AI systems face now, and the skills our sponsors look for when hiring or contracting red-teamers. They also directly connect to techniques you'll need for our upcoming prized competitions, so you’ll get a leg up when big prize money is on the line.
Showcase your skills.
Every completed challenge strengthens your Gray Swan profile:
Verified performance metrics
Shareable achievements
The expert-backed credibility that employers trust
We've already connected dozens of participants to contracts and jobs. With the Proving Ground, we’re making that pipeline wider and more accessible.
New to Red-Teaming? No Problem.
Some of our best red-teamers started with zero formal background. Writers, lawyers, students, and anyone curious, creative, and a little bit devious can find a foothold here.
You don’t need to code like a pro. You just need to think like an attacker.
Build the Future of AI Security
The Proving Ground is more than weekly reps. It's a growing arsenal of real-world techniques. A launchpad for new careers. A chance to stay sharp and get discovered.
Whether you’re just getting started or looking to level up, this is where red-teamers prove what they’re capable of.
🔥 First drop lands Wednesday, June 25.
Ready to earn recognition that matters? Enter the Proving Ground.
FAQs
Who can participate?
Anyone! You don’t need a CS degree or security background. If you're curious and love figuring out how things break, you're in the right place.
How often are the challenges released?
New challenges drop every Wednesday, starting June 25. You can jump in anytime.
What if I miss a week?
No problem! You can access past challenges in our permanent library.
Is it free to join?
Yes. Participation in The Proving Ground is free.
How do I access the challenges?
Challenges are available via your Gray Swan account.