Over the past 2 decades, the number of children with parents in prison has increased substantially. Using structural equation modeling with prospective longitudinal data gathered as part of the ongoing Linking the Interests of Families and Teachers (LIFT) trial, the study tests a theoretical model which examines the direct and indirect relationships of four specific domains (parental incarceration, social advantage, parent mental and physical health, effective parenting) as they relate to youth antisocial behavior in the 5th, 8th, and 10th grades. Across all three grades, the relationship between parental incarceration and youth antisocial behaviors was mediated through a complex set of both direct and indirect pathways involving social advantage, parent health, and effective parenting. The total amount of variation explained by the models for youth externalizing ranged from .60 (in 5th grade) to .21 (in 10th grade). The total effects in all the refined models were small.