The numbers of children under the age of 18 being incarcerated in England and Wales has decreased of late, with official figures indicating that the current population of just over 1500 has halved during the last decade. But levels of reoffending among children released from prison remain the highest, with three out of four young people being reconvicted within one year of release from juvenile custody. Despite the fact that the overwhelming majority of community-based sports projects target children and young people, when it comes to incarcerated populations, sporting initiatives are less prevalent. Where sport has become well established as a useful social cohesion/inclusion strategy in community settings, some of these approaches have been translated into custodial settings. Resulting research has often proclaimed sporting pursuits as a modern-day panacea in terms of their social, psychological and emotional benefits, yet few studies have explored the nuances of sports-based interventions within secure settings. This paper comprises a small-scale, qualitative study of one such intervention in a Young Offender Institution in the South of England. Placing respondent accounts at the centre of the analysis, the paper sheds light on the practicalities of programme delivery by uncovering the motivating factors behind participant engagement whilst exploring broader notions of personal development. The paper concludes by highlighting that sport/physical activity can confer significant psychosocial benefits and promote the rehabilitation of young people leaving custody, particularly when integrated into wider programmes of support and provision.