This presentation explores our current prison education system, opportunities and limitations to teaching theatre and playwriting in a prison setting, and what must change in order to make this work more equitable and enduring. Participants will learn best practices, unfortunate practices, and sustainable practices for keeping theatre front and center in the lives of those who are incarcerated. While the use of theatre as restoration is considered, the focus of this presentation is on the demands and expectations our theatre students have of us; the theatre community on the outside. How do we help these students grow as artists on the inside and prepare to welcome them into our educational and artistic communities once released?