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We advance prior research on the intergenerational consequences of legal system involvement through a mixed-methods study of college participation following a childhood experience with maternal or paternal incarceration. First, we conduct quantitative analyses using survey data of young adults from the Future of Families data, linked to their individual administrative records on college enrollment and graduation. We test the association of parental incarceration by age 9 with college participation by age 22 and assess the extent to which this association varies by the parent's gender and involvement in their child's schooling. Second, we analyze interview transcripts from a subsample of young adult participants and their primary caregivers to explore potential mechanisms for the association between parental incarceration and college participation. We consider theoretical frameworks of childhood socialization, system avoidance, and parental gender roles to contribute to our understanding of prison’s reverberating impact on the next generation.