This paper examines schooling inside a youth prison. We draw on interview and observation data from a study of a youth prison school to understand the practices and tensions of schooling in a juvenile incarceration facility. We describe the processes of schooling in the facility with an eye towards understanding both the conditions of learning and the ways that the prison context affords or constrains student learning opportunities. We describe several key features of schooling in a youth prison, which include: physical context and classroom settings; institutional emphasis on safety and control; the stigmatization of students; student transience due to movement through the legal system; disconnection between incarceration school and the school they attended before imprisonment. Possibilities of youth prison education to be transformative are also discussed.