Explore the intricacies of organizing and competing in Capture the Flag (CTF) hacking competitions in this 22-minute conference talk from USENIX Enigma 2016. Delve into the challenges of running contests for skilled computer hackers, including team building, contest design principles, and maintaining momentum across events. Learn about the differences between CTF organizing teams, competing teams, and modern commercial devops teams, as well as how these groups evolve over time. Gain insights into various CTF formats like Jeopardy and Attack-Defense, their scoring systems, and game dynamics. Discover the science and art behind creating effective challenges, considering team sizes and player experiences. Understand the operational aspects of different CTF types, hardware requirements, and how to handle exceptions. Examine the importance of empathy in challenge design, managing player frustration, and preserving agency and enjoyment throughout the competition.