It’s a lovely morning in the data center and you are a horrible ~goose~ devop. What sorts of trouble can you cause? For years, configuration management has been touted as a way of guarding against the fragility that comes from having humans configure things manually, but it isn’t a complete safeguard against things going wrong. In this talk I’ll cover the evolution of configuration management strategies used by operators to increase system robustness and will share stories about the ways that even mature management practices can fail. I’ll also discuss the underlying problem from a human factors and resilience engineering perspective, ways to further increase the reliability of our tools, and how those tools may keep evolving.