This study examines the ways in which playwriting and performance provide tools for incarcerated and formerly incarcerated girls to prepare for their lives beyond detention centers and probation. In a three-year multi-sited ethnography journeying through regional youth detention centers (RYDCs), a multi-service center serving formerly incarcerated youth, and a public theatre housing a women-focused theatre company in the urban southeast, this study raises questions about the gendering of the school/prison nexus and interrogates the role of programs. Ultimately this study urges scholars, activists, and youth advocates to combine efforts in coalition building to meet the needs of girls in under-served and under-resourced communities and schools. (Contains 2 notes.)