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Arrest in adolescence can adversely impact developmental trajectories. The consequences of juvenile arrest for educational attainment and continued system involvement in early adulthood are particularly concerning considering that these developmental disruptions may contribute to a process of cumulative disadvantage that extends over the life-course. Yet, the influence of juvenile arrest is not constant across adolescents. The purpose of this study is to examine how early life-family disadvantage affects the relationship between adolescent arrest and early adulthood outcomes. This research uses data from the Future of Families and Child Wellbeing Study (FFCWS), propensity score matching methods, and regression analyses to assess the differential impacts. The implications of this research for studying variation in the effects of adolescent arrest on later life outcomes are discussed.