CCDC (Collegiate Cyber Defense Competition) competitions ask student teams to assume administrative and protective duties for an existing "commercial" network - typically a small company with 50+ users, 7 to 10 servers, and common Internet services such as a web server, mail server, and e-commerce site. Each team is scored on their ability to protect their network, keep services running, and handle business requests while balancing security needs with business needs. This presentation goes over the journey of joining the 'other side' of these competitions: the red team. This team consists of industry professionals volunteering their time for the sake of security education and maybe have a little fun on the side too. We'll discuss the challenges faced hacking college students and the tools created as a response along with funny stories and incident reports filled out by students. We'll discuss zero day vulnerabilities found during the competition because of good blue teams and stubborn vendors. At the end you'll learn some red team antics and why CCDC is important to improving security education.