The numbers of youth in the U.S. with parents in prison is on the rise. Findings indicate that they are a vulnerable group of children. Using data gathered as part of the Linking the Interests of Families and Teachers (LIFT) randomized controlled trial, adolescents who had had an incarcerated parent are compared to those who did not across four areas: family social advantage, parent health, the family parenting strategies, and youth externalizing behavior and delinquency. Past parental incarceration was associated with lower family income, parental education and socioeconomic status, and parental health, and with higher levels of parental depression and youth problem behaviors and delinquency. The effect sizes for significant associations were small to moderate.