Several decades of research have shown that parental divorce can be a stressful experience for children and may lead to depression and other negative outcomes. Similarly, research has highlighted the stressors often induced by stepfamily formation and their effects on children. Although singular family transitions can exert influence, few studies explore how the combined stress from two family transitions may interact to influence long-term outcomes. Our study addresses this gap by using national data from 1142 respondents who experienced parental divorce and a subsequent transition to stepfamily life. Congruent with prior research, we find that retrospective reports of divorce and stepfamily stress is associated with higher depressive symptoms in emerging adults (18–30 years of age). We also find that stress induced by parental divorce and subsequent stepfamily formation significantly interact to increase depressive symptoms in this population. The research and clinical implications of our findings are discussed.