This chapter investigates the New Orleans Prison School—a public school in a prison—where African American male students were sent as punishment for nonviolent status offenses. Through the voices of local residents, including students and their families, teachers, local activists, and law enforcement officials, it explains what the push-pull factors of punitive schooling mean for their lives and their community. The chapter situates this examination in the historical context of urban school failure, youth criminalization, and mass correctionalization from the post-civil rights era of New Orleans forward. The work is theoretically framed by scholarship in the sociology of punishment, which articulates mass incarceration as a disappearing act playing out on the stage of the postindustrial and neoliberal state. The chapter ends by returning to New Orleans in the aftermath of Hurricane Katrina. While the city's schools were physically demolished by the tremendous floodwaters, the punitive ideologies of the city's criminal justice system remained intact. These ideologies resurged and were made manifest as the school system was rebuilt.