This thesis situates the Inside-Out Prison Exchange Program within the larger realm of postsecondary prison education to analyze its unique pedagogical approach. Through utilizing critical theory and other pedagogical theories, I will address several key themes in the Inside-Out Pedagogy including 1) humanization 2) dialogue 3) mutuality, and the way these frames and tools are used to approach questions of identity, criminality, and power dynamics within the classroom. In providing both benefits and limitations of the Inside-Out program’s efforts to facilitate dialogue across difference, I argue that Inside-Out moves beyond prison education frameworks rooted in recidivist and neoliberal paradigms and instead fosters opportunities based on empathy, critical thinking, and holistic growth and transformation. I also argue that some of the projects and frameworks of transformation, equality, and humanization are oversimplified. Overall, I argue in favor of college-in-prison programs like Inside-Out that can supplement pre-existing postsecondary prison education programs.