March and April 2012, I worked with ~80 security professionals, in remote and local contexts, to break into systems protected by ~500 active defenders across several events. In this talk, I share my experiences from the 2012 Cyber Defense Competition season and use them to analyze Armitage as a red teaming platform. Collaboration, automation, and distribution are discussed as opportunities to coordinate, scale, and protect red efforts. This talk is not about individual features. It's an exploration of how red teams organize themselves, what does and doesn't work, how we work around our tools, and what we need next. Those interested in the future of collaborative hacking should attend this talk.