This research focuses on a small group of female offenders in England and the ways in which engagement in the arts during incarceration can support and accelerate the desistance process. In the most recent review of the female prison estate, Robinson (2013) suggests that ‘life’ and ‘independence’ skills should be acquired in prison in preparation for release. Communication and social skills form the basis of many of the mainstream intervention programs within the Criminal Justice System (Caulfied & Wilkinson 2017:20). Expansion of independence skills would support the other skills that women learn in prison and offer a very practical response to the difficulties that they describe in their lives in the community (Robinson 2013). This research explores whether access to the arts within prison can form the basis of fostering such skills in order to motivate and engage learners. The transition from ‘offender’ to ‘ex-offender’ is considered, as are the ways in which agency acquired through the arts can be applied throughout the continuing stages of rehabilitation. By following a woman’s journey upon release and her integration back into the community the study determines whether the arts can sustain to the final stage of the desistance process, when someone creates a replacement self. The case studies of six women serving sentences at the same prison between 2012 and 2014 form the basis of this research, with their stories and experiences being told through their artwork and interviews. A criminological model of desistance developed by Giordano et al. (2002) contextualised alongside Margaret Archer’s (2003) theory of identity formation is critually evaluated. Links and comparison between evolving reflexive identities and transitional stages of desistance are presented in order to answer the research questions. In doing so, it is determined as to whether identity subgroups bare resemblance to specific stages in the desistance process. Critical analysis considers whether an individual can develop or re-establish an identity as a result of the creative activities they engage in during incarceration.