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Utilizing three survey waves of the Delaware Prison Research and Innovation Network (PRIN) project, we investigate how perceptions of programming, fairness, and prison climate impact self-reported reentry preparedness. Correctional practices and prison activities play a significant role in how incarcerated people feel about returning to free society and their potential for success in desistance, finding employment, and meeting personal goals. A supportive prison climate, characterized by positive institutional relationships between staff and incarcerated people, access to rehabilitative activities and programming, and fairness, can foster confidence in reentry preparedness, while a punitive or resource-deficient environment may undermine it. Results from this study will help inform correctional policies and administrations that seek to enhance reentry readiness. Strengthening reentry preparedness not only benefits incarcerated individuals but also contributes to broader community reintegration efforts and community safety.