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Prison education programs, often positioned as transformative and rehabilitative, can inadvertently reproduce harm through institutional constraints, selection processes, and power imbalances between inside (incarcerated) and outside students. This research critically examines the experiences of harm within the Walls to Bridges (W2B) program, highlighting the ethical complexities embedded in student selection, institutional surveillance, and classroom dynamics. Drawing from participant reflections, it explores how outside students navigate anxieties about causing harm, the ways in which privilege manifests in classroom interactions, and how institutional policies and practices shape the experiences of both inside and outside students. By exploring the intersections of security, education, and harm reduction, this research contributes to broader discussions on the limitations and ethical implications of education in carceral settings.