Explore the insights gained from writing Capture The Flag (CTF) challenges in this 43-minute conference talk from BSides Tampa 2017. Delve into various aspects of CTF challenge creation, including Jeopardy-style and Attack-Defense formats. Learn about the original goals, the "Thousand Cuts" approach, and the importance of integration testing. Discover the CTF challenge process, framework, and deployment strategies. Examine software goals, focusing on competition utility, educational value, usability, and the complexities of reliability. Understand the application of Twelve Factor App principles to CTF challenges and the significance of operations automation. Gain perspective on shared state management, debugging processes, and the importance of respect in challenge development. Recognize that building CTF challenges is a form of software development, with reliability imposing constraints and respect serving as a fundamental principle.