Despite less than optimal conditions, correctional classrooms provide a unique opportunity to make an impact on a student population often overlooked and avoided. Although there is a great demand for prison educators, attracting and retaining qualified teachers remains a constant challenge for prison school administrators. This mixed-methods study examined the problem of teacher turnover in one correctional facility to determine internal and external characteristics that likely contribute to teachers' decisions to stay or leave. Commonalities and differences of short-term and long-term teachers are highlighted, contributing factors are shared, and implications for prison educators and administrators are discussed.