Parkour/freerunning is a training method for overcoming physical and mental obstacles, and has been proposed as a unique tool to engage youth in healthy leisure activities (e.g., Gilchrist & Wheaton, 2011). Although practitioners have started to utilise parkour/freerunning in programmes for youth at risk of antisocial behaviour, this claim is insufficiently grounded in theory and research to date. In fact, the common misrepresentation of the practice in the media has led to confusion and debate about the nature of parkour/freerunning. In a conceptual and historical analysis, I explore what parkour/freerunning is, and how it can impact on the practitioner. Results from the analysis reveal values, goals and assumptions that parkour/freerunning is built upon, as well as a set of physical, mental, socio-moral and cognitive-behavioural skills developed through the practice. As illustrated by its history, parkour/freerunning has emerged as a highly versatile tool for self-development and change. These insights are used to discuss how parkour/freerunning relates to contemporary frameworks of offender rehabilitation. A comparative analysis demonstrates that parkour/freerunning is largely capable of meeting the standards of rehabilitation practice guided by the Risk-Need-Responsivity model. Moreover, key goals, assumptions and general approach in parkour/freerunning are naturally in line with those in the Good Lives Model of offender rehabilitation. The major overlaps of parkour/freerunning with both frameworks suggest that the practice can increase the individual’s capacity to live a healthy and prosocial life, and reduce the risk of reoffending. Particularly when applied within the GLM, parkour/freerunning offers a pathway to identity formation and transformation. Although this claim is in need of further exploration, I propose that parkour/freerunning can be utilised to enhance the practice of offender rehabilitation as an engaging and easily accessible tool for prosocial change.