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Existing literature speaks to the multitude of conditions placed on individuals under community supervision. Individuals on community supervision often characterize these conditions as emotionally, socially, and financially burdensome. However, little scholarship has addressed how these conditions may inform probation and parole officers’ views of compliance and community supervised persons’ perceptions of the criminal legal system. Our research aims to fill this gap and provide a deeper understanding of the tensions between individuals on supervision and those who supervise them while providing insight into the ways probation and parole officers manage discretionary decisions about compliance. We explore these issues through an analysis of in-depth interviews with probation and parole officers and people on community supervision in St. Louis, Missouri. Participants on community supervision often perceived that the system exists to extract financial resources from marginalized groups and linked resource extraction to supervision conditions. Though probation and parole officers spoke positively about their role in linking individuals with supportive services, they also highlighted myriad financial and social barriers to supervision success and sometimes criticized the punitive nature of conditions. We discuss the implications of these findings for work on legal cynicism and estrangement, as well as compliance with community supervision.