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This proposed presentation/paper describes a case study of a particularly unique partnership between a liberal arts institution and two types of correctional facilities: a medium-security state prison and a work release resource center. The partnership brought together undergraduate students together with incarcerated men to study as peers in a rigorous community seminar behind prison walls (Inside-Out). In addition, the presentation delineates how a liberal arts curriculum particularly, the utilization of particular texts, critical thinking skills in small and large group discussions, as well as group applied policy projects, linked academic learning to real-world problem solving. The result: students in a prison context were empowered to transcended “the prison label” and envisioned a new world of improved post-release opportunities for employment and participation in the larger society for themselves. Finally, with the experience of black male imprisonment now almost commonplace in many urban communities throughout this country, the significance of the vitally important contribution that American institutions of higher education in addressing questions of punishment and inequality can make is discussed.