The purpose of this article is to make an overlooked source of knowledge accessible to school teachers and administrators in order to challenge the prevalent discourse of cultural deprivation in urban schools and thus provide a more equitable education for all. Little is known about rich knowledge and self-education practices within prisons which could contribute to culturally relevant pedagogy as well as decrease the stigma of prison contact. Using portraiture methodology, we present a portrait of EL'YAH'el, a formerly-incarcerated African American man who participated in self-education in prison as both a student and a teacher. Framing our work with reality pedagogy, we contend that understanding the traditions of self-education in prison can provide clues for teacher education programs committed to acknowledging and building upon their students' realities. We suggest the flow of knowledge from prisons to schools as the "prison-to-school" pipeline and conclude with recommendations for pedagogy and policy.