This research focuses on an under-examined aspect of the post-release prison trajectory for a seldom-researched cohort. Narratives of the immediate days/weeks surrounding release were gathered from young men with histories of injecting drug use (IDU). Twenty-eight participants (aged 19-24) released from adult prisons in Victoria, Australia, participated in face-to-face in-depth qualitative interviews after release. Analysis of findings through the lens of a “risk environment” framework reveals how their experiences were compromised by risk factors embedded in the physical spaces and social situations they inhabited, as well as the multi-sectoral policy environments under which they were governed. A complex interplay between these factors, young men’s drug use and broader issues of structural vulnerability, including institutionalization and social disadvantage, combined to limit young men’s chances of “success”1 on the outside. Narratives provide evidence for interventions that transform risk environments into enabling environments, thereby promoting a more successful transition from prison to community for young men with IDU histories.