Using data from a 6-year longitudinal follow-up sample of 240 youth who participated in a randomized experimental trial of a preventive intervention for divorced families with children ages 9–12, the current study tested alternative cascading pathways by which the intervention decreased symptoms of internalizing disorders, symptoms of externalizing disorders, substance use, and risky sexual behavior and increased self-esteem and academic performance in mid- to late adolescence (15–19 years old). It was hypothesized that the impact of the program on adolescent adaptation outcomes would be explained by progressive associations between program-induced changes in parenting and youth adaptation outcomes. The results supported a cascading model of program effects in which the program was related to increased mother–child relationship quality that was related to subsequent decreases in child internalizing problems, which then was related to subsequent increases in self-esteem and decreases in symptoms of internalizing disorders in adolescence. The results were also consistent with a model in which the program increased maternal effective discipline that was related to decreased child externalizing problems, which was related to subsequent decreases in symptoms of externalizing disorders, less substance use, and better academic performance in adolescence. There were no significant differences in the model based on level of baseline risk or adolescent gender. These results provide support for a cascading pathways model of child and adolescent development.