Parental incarceration has been found to be associated with a wide range of negative outcomes in both childhood and adolescence. This Article uses data from the National Longitudinal Study of Adolescent Health (Add Health) to focus on the conditions under which associations of paternal incarceration with adolescent delinquency and depression are strongest. Paternal incarceration is most consistently and positively associated with adolescent delinquency. Associations of paternal incarceration with adolescent depression are weaker and more contingent on gender and other moderating factors. One important moderator is the respondent's retrospective reports that he or she was physically or sexually abused by a parent or other adult caregiver during childhood. For example, in the absence of sexual abuse, paternal incarceration is associated with higher depression among girls. When coupled with reports of sexual abuse, in contrast, paternal incarceration is not associated with girls' depression, suggesting a potential protective effect. The child having ever coresided with his or her father is also found to moderate associations, with paternal incarceration most strongly associated with delinquency and depression among girls who had ever coresided with their fathers. Examination of the duration and timing of paternal incarceration also pointed to gender differences.