This paper considers experiences of penal and voluntary-sector interventions in the lives of young people labelled as ‘troubled’ or ‘at risk’ of criminal behaviour. Drawing on data from a case-study conducted in the north of England, this paper focuses on the narratives of young people ‘on the margins’ of society who were involved with a range of community-based interventions, specifically youth clubs, a support group and a mandatory youth justice course. We consider how young people experience and respond to stigmatising elements prevalent in the structured interventions and everyday interactions with the institutions and agencies intended to support them. We argue that ‘promotive’ relationships between young people and the adults working with them enable young people to challenge risk-based identities and navigate the barriers they face.