This chapter provides an overview of rehabilitation and desistance-orientated uses of digital tools and approaches in prison and probation settings. Considerable attention is often given to ‘what’ established and emerging technologies can do in criminal justice. Yet ‘how’ and ‘why’ such technologies are used and advanced, by whom and for whom remain indispensably important. ‘Digital justice’ and digitally enabled supports for rehabilitation are explored here, reflecting on their potential, alongside considerations of purposes and practicalities of implementing them. Monitoring and reporting technologies can be differentiated from technologies which are more therapeutic and rehabilitation-orientated in their uses; this chapter concentrates on the latter. International literature and practices are incorporated throughout, however, the chapter purposely focuses on applied examples from England and Wales, including a co-produced digital toolkit using animation in prisons and probation contexts.