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Unlike incarceration, which removes people from their communities, probation and parole employ mechanisms of control and surveillance in non-institutional contexts. Simultaneously, community supervision has also become a site of treatment referral and resource brokerage, fundamentally intertwining punishment and welfare functions. As a result, how these play out together on the ground, particularly for probation/parole staff tasked with fulfilling these roles, is likely shaped by the spatial and social contexts in which these staff work. To explore how structural and interpersonal practices across place influence probation/parole agents’ perceptions and work, this study draws from semi-structured, in-depth interviews with 60 probation/parole agents working in one Midwestern state in the U.S. Comparing places across the rural-urban continuum, I find that, while agents in varied communities across the state view their roles and expectations of their work similarly, in practice, the differing structural and social conditions of rural, semi-urban, and urban counties impact daily operations. Stratified resource availability and access as well as the heterogeneous organization of ties with other criminal justice system actors both impact agents’ work on the ground, ultimately complicating the implementation of statewide policy and practice in counties across the rural-urban continuum.