Postsecondary programs offering vocational training and college credit to eligible inmates have had difficulty finding a place in the U.S. correctional system. Politically motivated restrictions preventing inmates from receiving federal funds for college resulted in drastic program closures. Although new laws restored funding to select inmates, enrollment in postsecondary correctional education only recently reached pre-cutback levels (established in the late 1980s). This is set in contrast to the significant increases in U.S. prison populations and spending that have occurred since the early 1990s. Contextual issues specific to the correctional system and ideological conflicts between the prison educator and prison staff may further impair enrollment and program completion. Through review of the political and contextual issues influencing the modern design of postsecondary prison education, this work seeks to propose best practices that may support the unique learning needs of the adult learner in the correctional system.