The text analyzes the processes of education in the penitentiary setting, with particular attention to the experiences of Penitentiary University Poles, in order to investigate how the reeducative function that the Italian Penitentiary Order aims to pursue can be implemented through university study. How Penitentiary University Poles can be an opportunity to revitalize the re-educative function of punishment is investigated. In particular, the first two Penitentiary University Poles established in Italy will be analyzed: that of Turin and Prato. Testimonies from teachers in prison and student inmates will also be voiced, stating how these initiatives can open the doors of the prison and allow contamination between inside and outside. The intent is to demonstrate how the antithetical university-prison binomial can take on a liberating role within a space of confinement, allowing inmates to rediscover their role within the complexity of society and strengthen their sense of belonging and citizenship, promoting the personal, social and cultural growth of each individual.