This narrative inquiry research study examined the impacts and outcomes that postsecondary education, even if not completed, had on individuals with criminal records once they have reentered society. While quantitative studies show the positive relationship education has on reducing recidivism, less research has been conducted examining why it has this effect. This study explored the experiences of five African American men who had been convicted of a crime and who later participated in postsecondary education courses. They interpreted that experience and its impact on their experiences post-release. Participants were chosen using purposeful sampling. Data was collected through a semi-structured interview, consisting of one interview of each participant lasting 60-90 minutes. Critical race theory and counter-storytelling was used to analyze the experiences and to interpret what if any impact race has on experiences with education and reentry. Finally, there was a discussion of larger themes comparing it to established literature. Reflecting on the study, recommendations were made for educators, future studies and others preparing for life post-release.