The security and devops culture craze is all around us, even with all this talk though there are differences between security features and the maintainability of a system. This talk will focus on some real world examples of what can go wrong when a system isn't built with maintainability in mind in a security minded culture. We will cover the political positioning battles that emerge, how security leaders can manage risk in these situations, and of course the technical challenges that creep into the picture over time.