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Youth experiencing incarceration are removed from home communities, separated from family members, and disconnected from school—factors that have been found to play a role in continued delinquent activity and impact developmental transitions required for youth to become successful adults. Existing research literature, while acknowledging various risk and needs factors of youth in the justice system, is limited in its understanding of the processes underlying youth reentry. Working within a developmental framework, qualitative methods were used to construct life histories for youth who had been incarcerated and have made the transition to the community. This presentation will discuss three categories of youth that emerged from the data—youth engaging in delinquency as a way to cope with anger; youth drawn to a “street” culture and gang involvement; and youth with supports who have fallen victim to peer influences. The similarities and differences between each type will be discussed within three phases: the pathways they took to placement; their experiences and perceptions of placement; and how that experience impacted their transitions home. Gaining better understandings of these mechanisms for youth is useful for policy makers to develop juvenile justice services that are responsive to their developmental needs.