Objectives: This article examines the influence of social context on punishment decisions. To this end, we present a theoretical framework to identify outcomes that can occur when police and probation officers work in schools. Method: The proposed framework draws on organizational theory as well as scholarship on school discipline and punishment and the effects of placing officers in schools. It also draws from insights gathered from site visits, interviews, and focus groups conducted as part of a process evaluation of a school-based delinquency prevention program. We then present data from interviews and focus groups with 41 school-based safety staff to examine the plausibility of the hypothesized framework. Results: We find that officers’ goals interact with the goals of school-based actors to influence punishment-related outcomes. We also find that officers are not always the more punitive force in the schools and that placing officers in schools may have positive as well as negative effects for youth. Conclusions: The findings suggest that current accounts of officers in schools are incomplete. Dynamic interactions may occur within organizational partnerships and should be considered when seeking to understand punishment decisions not only in schools but also in other settings.