Applications for funding for arts interventions in prisons need to show the intervention will be working towards reducing reoffending. Previous studies mainly focus on the rehabilitative results of the arts intervention in repairing deficiencies in offenders’ social skills. These deficiencies prevent offenders from making constructive social interactions and are proved sometimes to be characteristic of criminality. However, the aim of this investigation was to use a grounded theory methodology to deconstruct the link between arts and rehabilitation by engaging in a research study in a young offender’s institute (YOI). The findings from the pilot study revealed that the link between rehabilitation and the Arts emerged as its potential to enable the appropriation of new roles. Taking these findings into my literature review, I developed a core framework around rehabilitation, an intervention typology, the Arts and role theory. I took this framework into my main investigation in a YOI in South West England amongst young people involved in music and art courses. From later stages in my research design emerged the significance for young people of the use of autobiographical techniques, showing the potential for participants to gain emotional and cathartic release before moving to a consideration of their future. Further depth of understanding of this pedagogical strategy was gained through interviews conducted with those involved in another course using autobiographical techniques: the Write to Freedom course. The outcomes revealed the place of role in developing and affirming identity and the pedagogical influences which were necessary to enable rehabilitation. The findings add to understanding about pedagogical structures, which can help a young person to envision a new role in a future that embraces desistance. These findings have implications in other contexts where participants inhabit roles which prevent learning development. These techniques can change perception enabling participants to appropriate renovated roles which offer new direction.