Over the past several decades, the number of youth with parents in prison in the United States has increased substantially. Findings thus far indicate that they are a vulnerable group of children. Using prospective longitudinal data gathered as part of the population-based Linking the Interests of Families and Teachers (LIFT) randomized controlled trial, adolescents who had an incarcerated parent during childhood are compared to those who did not across four key domains: family social advantage, parent health, the parenting strategies of families, and youth externalizing behavior and serious delinquency. Past parental incarceration was associated with lower family income, parental education, parental socioeconomic status, and parental health, and with higher levels of parental depression, inappropriate and inconsistent discipline, youth problem behaviors and serious delinquency. The effect sizes for significant associations were small to moderate. (Contains 1 figure and 2 tables.)