The process of desistance is underpinned by criminal justice practitioners building positive relationships with offenders as well as recognising their individual skills, strengths and agency (McNeill & Weaver, 2010; McNeill et al. 2012). Recent reorganisations within probation services in England and Wales, as well as a broader austerity agenda have reduced the capacity for delivering group-based rehabilitation interventions depleted. Digital technologies have been suggested as possible way of developing new interventions to achieve the goals of desistance, though their use is currently limited and uneven across the sector (Knight, 2015). Other sectors, such as healthcare, have been more proactive in developing their use of digital technologies to support the delivery of services and treatment. This paper examines the potential of two approaches to utilising digital technologies currently in use by mental health services: personal digital assistants and self-guided therapies. The aim of the paper is to identify the potential for their deployment in a criminal justice context.