This research investigates and advances knowledge of the factors that shape the teaching role and hinder education delivery in the United States' jail system. This is an area in which little research has been undertaken. Correctional teachers work with incarcerated adults in jails and prisons. This research comprises a series of closely related investigative studies that critically explore historical, political, and ideological factors that determine the intent and purported outcomes of education programs in jails. This approach leads to a comprehensive case study of a jail correctional education program. In the course of the investigative studies I point to how correctional education has capitulated to penal trends and powerful political agendas that drive correctional and education policy, some of which appear to be diametrically opposed to the interests of teachers and inmate students. The findings leading from the case study point to why teaching in such a setting is logistically, institutionally and politically complicated, and excessively so. I elucidate how a preferred teaching role is constrained by a divisive workplace culture, a range of institutional problems and, not least, a complex inmate student population. These matters are magnified by convoluted education policies including high stake standardized testing. In the course of the case study, I provide examples of how teachers working in a jail setting attempt to navigate the many pressures and demands on their time armed with finite resources and an education model which in many respects defines their role as teachers