Paternal incarceration is an important predictor of teen delinquency, but the factors that may explain this relationship--such as early child problem behaviors and level of father engagement--have not been adequately explored. The current longitudinal study examined paternal history of incarceration as a predictor of teen self-reported delinquency over a 15-year gap, considering early child problem behaviors and father engagement as mediators. Sex differences in these relationships were also evaluated. This four-wave longitudinal study included an analytic sample of 4897 teens who participated in the birth-cohort Future of Families and Child Well-Being Study. Mothers and fathers were interviewed shortly after the focal child's birth and were then reassessed in follow-up interviews at child ages 1, 3, 5, 9, and 15. The focal children were interviewed at ages 9 and 15. Results showed that paternal prior incarceration at year 1 was associated with greater child behavior problems and father engagement at year 5; however, those relationships disappeared by age 9. Paternal history of incarceration was not related to teen delinquency, but child behavior problems at age 9 were directly related to subsequent engagement in delinquent behaviors. Paternal current incarceration was related to subsequent father engagement but was not associated with later child behaviors. No significant indirect pathways emerged, indicating a lack of support for mediation. No sex differences in these relationships were observed. Overall, the findings underscore the complexity of the relationships between paternal incarceration, child behavior, and father engagement in the emergence of delinquent behaviors.