This dissertation examines restorative justice in a large public school and the labor of shifting the school’s punitive discipline culture to one that is restorative. It investigates how school staff experience this shift and what their experiences tell us more broadly about how practices of punishment and care interact, and how these practices reproduce or contest the dehumanizing racial conditions of urban school life. Extolled as one of the best interventions to address discipline disparities and transform school cultures of violence, restorative justice has become a central social justice effort to disrupt the link between schools and prisons in the United States. Punishment and Care explores how restorative justice was received during its implementation, and if restorative justice indeed offered alternatives to the criminalization of children. Ethnographic observations and in-depth interviews with non-profit restorative justice workers, school security officers, teachers, and administrators, reveal how well-intentioned adults bring the paradoxical relationship of discipline and care to life. Analyzing discipline, criminalization, and care as mutually constitutive rather than opposed processes in the work of school staff, it focuses on people who brought strong ideals to the work of school culture change and how these ideals were forgotten. This dissertation treats real life circumstances as complex and contradictory, ultimately making apparent the ways that punishment and care become symbiotic priorities in educating poor children, rather than the work of education itself.