The prisoner constituency is one of the most excluded in society. Addressing recidivism requires amongst other considerations, an enabling of these individuals to fulfil rehabilitative intent. The article argues that this necessitates an educational discourse and methodology that is embedded in concepts of emancipation and empowerment, where creativity and heuristic learning enable personal transformation. The arts are one of the agents that can naturally encourage spontaneous and participatory learning, enabling a more liberating and self-directed rehabilitative process. Notwithstanding, arts education in prison illuminates the struggle between individual creative needs and social accommodation. Historically the shifting paradigm of penal policy has reflected a wider political intention. But there is an irony as the New Labour government that champions social inclusion has overseen the reduction of opportunity in prison to engage with the arts, replaced by an instrumental agenda concerning basic, key and cognitive skills. Furthermore, this has arguably been costly and ineffectual, hence the need to accommodate a more creative and expressive curriculum. The article has been divided into two parts. The first examines competing discourses of penal educational provision in order to assess the role of the arts. The second part examines a radical educational agenda of inclusion based on emancipatory theory, as a conduit for personal transformation, in which the creative arts have a central role.