This article introduces post-carceral treatment and supervision in the Costa Rican Penitentiary System. It focuses on two programs for prisoners who apply for early release and continue to receive professional intervention until the completion of their sentence. Interviews to Costa Rican penitentiary officers from two regional offices in the Puntarenas Province were conducted in 2021 to determine the characteristics of day-to-day supervision of former prisoners benefitted with early release. From the results of the interviews, it became clear that Costa Rican penitentiary work is highly specialized and discretionary. In the future, a comparison of the degree of specialization and discretion with other jurisdictions will help elucidate how penitentiary work influences the outcome of penitentiary treatment in community settings.