Many jurisdictions are currently experiencing the effects of “mass supervision,” managing record-breaking numbers of people on probation and parole orders. Despite large numbers of people supervised on community corrections, little is understood about how these individuals navigate their supervision and their efforts to refrain from reoffending. In this article we analyze interviews with 53 probationers and parolees about their experiences with community supervision and their desistance journeys. Using an informant-by-variable matrix, our findings demonstrate that these community-supervised correctional clients generally want to steer clear of crime opportunities. The participants described how they utilized individualized and targeted strategies to reduce, resist, and replace these reoffending risks, recruiting handlers to help facilitate or encourage the use of these strategies. These results showcase the utility of opportunity-reduction models of supervision, contributing to our understanding of the decision-making processes of individuals subject to community corrections orders.