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The Biden Administration’s Safer America Plan, Second Chance Pell Grant Expansion, and Alternatives, Rehabilitation, and Reentry Strategic Plan highlight the societal consequences of unsuccessful reentry and promote education as a strategy for creating safer communities. A meta-analysis in Prison Legal News indicated that prison-based education “resulted in a significant decrease in recidivism for prisoners” (Sanders, 2023, p. 44). The Vera Institute posits that participation in postsecondary education lowers recidivism risk by 48% (2024). The literature is also replete with examples tying carceral-based education to lowered post-release unemployment, reduced housing insecurity, and lowered correctional spending (Stickle & Schuster, 2023). Clearly, society benefits exponentially from educational programming in prisons. In the midst of lauding education for enhancing societal safety and well-being, it is easy to overlook the impact of educational opportunities on the incarcerated individual. Using the teachings of Paulo Freire as a springboard, this roundtable examines the transformative impact that prison-based education can have on students. Social work professors at a Midwestern university examine how they leveraged teaching a Human Diversity and Social Justice course in a prison to counteract experiences associated with carceral institutionalization. The presenters explore Freirean strategies for using education to promote empowerment, autonomy, humanization, and hope.