Many historians of prison post-secondary education have explained its development as a function of the rise of the U.S. system of higher education in general. Along with their parallels in development, the relationship is examined for the variance between the experience of an inmate-student and a student attending classes at a college or university. This article identifies three key areas where the expansion of the American system of higher education has influenced the growth of prison education: (1) the rise of public and community colleges; (2) the domination of the liberal arts curriculum (arts, humanities, languages, social sciences and physical sciences); and (3) the implementation of the Pell grant program (allowing inmates who meet certain financial criteria to get Federal aid for college level courses). In addition to these areas fostering the development of prison post-secondary education, they may also have influenced it limitations including: (1) tuition increases; (2) prison educators with advanced degrees competing with their professional concerns; (3) the illegal reporting of higher tuition costs for additional Pell grant funds; (4) the increased interest in liberal arts in prison and the decrease interest by college students; and (5) the debate over the use of Pell grants for inmate education. In conclusion, it is noted that by automatically including prison higher education in the historic expansion of American higher education there is the opportunity to overlook its own distinctive history.