As designers we strive for simplicity and look to reduce complexity in systems. Very often we measure our own ability, and that of others, by this imperative. But what happens when offering real value requires complexity? What if you are designing for users who demand complex functionality? And how does a designer who has spent their career in the quest for beautiful simplicity deal with it. This talk offered insights based on work at Puppet, one of the world’s most successful configuration management tools that includes NASA, Marvel and CERN amongst its customers.