Generativity, defined as the actions of an individual or group that enable others to care in meaningful ways for themselves and their significant others, has become an important concept for thinking about desistance from crime. In this article, we explore opportunities for prison officers in metropolitan and regional South Australia to model and/or engage in generative conduct. We find the emergence of generativity to be idiosyncratic—linked to individual officer’s capacities to resist the dominant "us" versus "them" culture—and to be often thwarted by a fatalistic outlook. Correctional policy implications are discussed.