This article investigates the role of the arts in enabling prisoners to engage with learning and improve their literacy, and the impact this has on their rehabilitation and desistance from crime. It draws on data collected from prisoners who participated in arts interventions in three different Scottish prisons. It argues that participating in the arts projects built an active learning culture and encouraged the improvement of verbal and written literacy skills through the use of positive pedagogical approaches. In addition participants learned to work together more effectively, developed self-confidence and were more trusting and supportive because they were working together on intensive projects that they had co-devised. For many prisoners participation in the arts projects constructively challenged and disrupted the negative identities that they had internalised. Their public successes in performances before audiences of significant others opened up new personal and social identities (as artists or performers) that helped them to begin to envision an alternative self that in turn motivated them towards future desistance from crime.