This article presents interviews with six composition and rhetoric teachers who teach writing in prison. Mina Shaughnessy’s 1976 article “Diving In: An Introduction to Basic Writing” is used as a heuristic with which to look at this material. As little work is available on the experience of teaching writing in prison, these interviews are a preliminary step in describing and understanding this transformative experience. The differences between the prison writing teachers and the teachers Shaughnessy describes illuminates how much the field of composition has grown in the last forty years. The interviews with these six teachers speak to the experiences of teachers in community outreach teaching situations and may be a step in understanding and articulating these experiences