Legacy is California’s newest version of “continuation” or alternative education. This school is housed in a World War II army barrack. Here, kids are searched, made to walk through metal detectors, placed on formal or informal probation, and subjected to perpetual contact with criminal justice agents. In this school we find the Recuperation Class. This class is a self-contained program for youth with “drug dependence and other behavioral issues.” Unlike the rest of the school, the local probation department directly funds this classroom. In this unique setting, the teacher provides instruction as the probation agent walks around, conducts random drug tests on students, questions youth about their behavior outside of school, and/or takes them directly to detention. Legacy school officials have granted this criminal justice agency unfettered access to their students in return for financial support. While the probation department refers to this well-intentioned process as providing wraparound services to students, I argue that this process resembles “wraparound incarceration” where students cannot escape the formal surveillance of institutions of confinement. In this institution, young women move back and forth between this school and secure detention.