This article explores the role of cognitive transformations in the process of desistance from crime. Based on our own and others’ subsequent research, clearly, some aspects of our initial theorizing warrant revisiting and adjustment. The discussion describes changes to ideas about the sequencing of various types of cognitive shifts, suggests the importance of emotional processes in tandem with changes in perspective, and highlights the need to move out of the comfort zone of crime itself when thinking about redefinitions that support desistance. Yet, a consistent notion remains that social and broader structural factors are deeply implicated—directly and indirectly—in all aspects of the change process. This includes the important area of “derailments” from a pattern of forward progress, where additional processual research is needed. The discussion concludes with the argument that individualistic policies and programs centered on cognitive deficits requiring correction are likely to be limited in their effectiveness.