Ever wonder what it takes to build a information security competition? This talk covers the challenges of building competitions that challenge professions and students that stay fresh and relevant with the constant changes in the industry. This talk will cover the Western Regional Cyber Defense Competition and the efforts we have put into building a more realistic and challenge competition through custom tooling, infrastructure, and applications that we have been building into our competitions. Some of the things we will be covering include using modern tools such as Ansible in combination with our agent “Mr. Smith” which can allow for a highly scalable competition, and how to build and deploy usable ICS systems quickly for competitions.