I ran the DEF CON CTF from DEF CON 20 to DEF CON 25. Prior to that, I won a few.
I know order of the overflow is running a good game now. It’s different than what we did, but it’s a good direction, and I am hopeful it will continue to grow.
They (like we did) have a few selected prequalification events tbgat are generally pretty high quality. See https://www.oooverflow.io/dc-ctf-2019-quals/
PlaidCTF was an old favorite of ours as well. PPP has won several competitions, and seems to understand what makes a good challenge, what makes a challenge hard, and more importantly, what DOESNT make a good/interesting challenge.
Boston Key Party also runs a pretty good game. But a lot of them became Order, so who knows what will happen with them...
DARPA ran a CTF for autonomous systems called the Cyber Grand Challenge. It was neat, but I don’t know of any plans to do anything like it again. I believe they’re waiting to see what the community does to push the state of the art further. Source code for challenges and infrastructure are at https://github.com/cybergrandchallenge. There’s also a bunch of video at the darpatv YouTube channel.
We open sourced most of our challenges/frameworks after the fact. https://github.com/legitbs. This includes the compiler/emulator/manual for our 9-bit bytes custom architecture, clemency. That was probably our most ambitious year...
That’s all off the top of my head. If you care for more from a CTF has been, I’m happy to come back and answer more questions.