This article explores a unique approach to becoming literate about prisons ––through a dialogical exchange between individuals on both sides of the wall. The Inside-Out Prison Exchange Program offers a semester-long course through which college students and incarcerated men or women attend class together weekly inside a local correctional facility. Pivotal to this pedagogy is the power and reciprocity of the exchange between the “inside” and “outside” students. The depth of discussion involved, the collaborative nature of the engagement, and the consideration of the issues (literally from the inside, out)––together encompass an approach to learning that changes lives.