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Recent research and theory suggest that human agency and identity change are key factors that drive desistance from crime. However, precisely how offenders exercise agency and work towards a prosocial identity in the face of myriad structural barriers is an issue not yet settled. Further, the role of formal corrections in identity change and fostering capabilities to be agentic is not yet clear. This paper explores these issues through a grounded theory analysis of data obtained from interviews with eleven once-prolific male offenders who had since given up crime. Results indicate that these men made a rational choice to give up crime, based on the accumulating pains of incarceration and addiction, and subsequently made agentic moves to change themselves and their surroundings. While formal correctional programming did not seem to play a large part in these changes, participants described more informal programs as beneficial. Recommendations for correctional policy are discussed in light of these findings.