Researchers and policymakers have frequently endorsed the incorporation of social supports into the reintegration process, despite limited research about the effectiveness of such an approach. In this article, we describe an experimental trial and evaluation of Triple-S: Social Supports in Supervision. The project involved community corrections staff serving as ‘super controllers’ who recruited ‘PoPPs’ (parents/partners/peers of probationers and parolees) to serve in the crime prevention roles of handlers, guardians, and managers. While the program had several important benefits, our evaluations have revealed key lessons learned that may be of use to other penologists and corrections agencies.