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In January 2016, a small group of university students tentatively entered a classroom to be greeted by a circle of incarcerated young men. The exchange of polite handshakes and hellos appeared innocuous, but marked the culmination of 11 years of struggle to establish an Inside-Out course with academic credit at a metropolitan, Catholic university. This presentation examines the institutionalized structural forces countering collaboration between the university and jail, as well as the sources of support and commitment to transformative, experiential learning. Drawing on official documents, personal correspondence, and anonymous student writings, I explore how a shifting social context enabled the implementation of a course in one of Rikers Island’s 10 jails, and how the course has served to create new spaces for dialogue and social action campus-wide.