In recent years, scholarship has chronicled the role of probation in the rise of mass incarceration and has concluded that community supervision is a trap that routinely punishes the poor under the threat of incarceration. Starting in 2010, under a reform-minded new commissioner, the New York City Department of Probation (DOP) sought to roll back probation’s punitive role. In sharp contrast to the tough-on crime approach of previous decades, the DOP adopted the motto ‘Do no harm, do more good, and do it in the community’, and became the first probation department in the nation to spearhead a local justice reinvestment project. Its signature initiative was the decentralization of probation into a series of store front offices known as the Neighbourhood Opportunity Network, which embedded the agency more deeply into poor and working-class communities of colour. Relying on ethnographic research with probation officers, systems involved youth of colour, and non-profit organizations in the South Bronx, this article examines the limits of carceral humanism as a growing trend in recent criminal justice reform efforts.