Finding research on prison officers that does not emphasise their importance—even centrality—to prisons’ daily operation and to the implementation of prison ambition more generally proves almost impossible. Even so, depending on jurisdiction, uniformed prison staff’s portrayals range from ‘czars and gods’ to disempowered and hectored conductors of penal power that merely flows through them. Power lies at the heart of prison—prison is about power. In the current chapter, drawing on the case of Ukrainian prison officers, I discuss how officers in the same prison can understand and deploy their power differently. I underscore the limitation of presenting them as a dichotomy of a ‘powerful/powerless’ homogeneous group and explain how cultural legacies, legal and organisational ramifications of the anomic society in transition, and officers’ personal views, priorities, and considerations of legitimacy frame officers’ use of power. I highlight that even in a country where prisoners enjoy limited rights and the state grants staff enormous power, prison officers must inhabit their power carefully and maintain prisoners’ alignment to preserve workable order.