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Offenders released from incarceration during emerging adulthood face numerous challenges as they take on the responsibilities of adulthood while adjusting to community and family life. Research suggests that family contextual factors such as family conflict can have a negative impact on reentry, yet studies have also shown that families support returning offenders in ways that are critical to their reintegration, creating a paradox that is not fully understood. In-depth interviews were conducted with young adults released from incarceration and members of their families to explore the social processes of reentry and desistance. The data show that returning youth struggle to overcome pre-existing family problems but they also rely on family support. Several developmental processes are identified to explain how young adults access support in their extended family networks. An increased psychosocial maturity during the twenties leads to a greater appreciation for family and sense of family responsibility, changing the nature of family relationships. Some young adults reexamine and realign their family ties, allowing returning offenders to structure their relationships in ways that offer them support.