The dramatic growth of prison populations in the United States during the latter half of the twentieth century, as well as the problems of over-policing and police misconduct, have been well documented and decried.1 But the related expansion and problems of community supervision receive far less attention. Across the nation, reform efforts have increasingly included a focus on probation, especially juvenile probation, as an actor that both jails and polices youth in the community while also trying to rehabilitate them and promote their well-being. This Article studies the juvenile probation system, with a focus on California as one important system aiming to both surveil and care for individuals. It draws together two frameworks: 1) law and policy which describe the juvenile probation system as intended, and 2) juvenile probation practices and attitudes which reveal the day-to-day translation of the system’s formal intentions. Ultimately, where a system’s approach to rehabilitation and accountability become synonymous with or too reflexively able to adopt surveillance, containment, and punishment orientations, its ability to deliver meaningful help and support through that same system is improbable. Thus, this Article discusses the need in the United States to reform, dismantle, or replace probation with youth development-focused systems and uses Los Angeles as an example of a government already doing this important work. 1 Cecelia Klingele, Rethinking the Use of Community Supervision, 103 J. Crim. L. & Criminology 1015, 1018 (2013).