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The period of years between ages 15 and 25 is one in which many crucial life-course transitions occur across multiple domains, including education, labor force participation, and personal relationships. Incarceration during these years interrupts and distorts these transitions and sets up barriers to successful reentry into the community. These challenges are likely to vary considerably based on experiences prior to incarceration, the nature and duration of the incarceration, and the considerable differences in psycho-social maturity between individuals and between younger and older persons within this age range. Drawing on the three ongoing qualitative studies of reentering youth and young adults described in the other papers in this panel, this paper proposes a comprehensive framework for investigating the social processes that connect transitions in family and peer relationships to the challenges of reentry from incarceration. Particular attention is directed towards the need to connect the larger structural context of changes in the timing of labor market entry, marriage and childbearing across society to the community-specific contexts of highly disadvantaged communities in which most incarcerated young people have grown up and to which they return after incarceration.