This qualitative research project aims to evaluate the Inside-Out Prison Exchange Program through the lens of prison education and desistance. This project is unique in that it uses a secondary dataset collected from a Think Tank consisting of both incarcerated and nonincarcerated former Inside-Out students alike. Using Grounded Theory to analyze the feelings of the participants and the attitudes toward the program, I apply the theories of desistance and a realist model of prison education, growth, and desistance to concepts defined in the desistance process. Overall, the results are positive and suggest that the Inside-Out Prison Exchange Program can operate as a catalyst for the desistance process, further contributing to the conversation of prison and education.