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My project explores the history of higher education in Massachusetts prisons in the broader context of the American carceral state. Educators, politicians, advocacy groups, and students themselves pioneered access to college coursework for incarcerated students in Massachusetts. Their work established some of the longest-running and most successful college-in-prison programs in the country, building on the potential of higher education to disrupt trends in mass incarceration, particularly along racial and economic lines. Long positioned as a bastion of liberal ideas and educational excellence, Massachusetts provides a unique lens through which to view the history of college-in-prison. Building on work other scholars have offered regarding the disconnect between the Commonwealth’s reputation and the ways that predominately white residents have responded to more progressive legislation, my dissertation explains how college-in-prison was situated in the middle of a political frenzy centered on race, education, and corrections. From the Boston busing crisis in the 1970s to the prison furlough program controversy of the 1980s, Massachusetts stood at the crossroads of liberal policy and virulent public opposition. As a tough-on-crime agenda swept the nation in the 1990s, the impact of the sweeping 1994 Violent Crime Control and Law Enforcement Act seemed to doom college-in-prison programs. In Massachusetts, at least one managed to survive. Weaving together a blend of media sources, documents from state archives, and personal narratives from educators, students, and college-in-prison program leaders, this dissertation documents the long and tempestuous struggle to bring higher education to incarcerated students in the Commonwealth of Massachusetts.