Guided by the family systems theory (Cox & Paley, 1997) and emotional security theory (Davies & Cummings, 1994), the present study examines multiple mediators linking parental depressive symptoms and adolescent behavior problems. Participants were 273 adolescents (133 boys, 140 girls) and their cohabiting parents. Assessments included mothers' and fathers' depressive symptoms and family emotional expressiveness when their adolescent children were in 7th grade, interparental and family conflict and emotional insecurity when the adolescents were in 8th grade, and adolescents' internalizing and externalizing problems in 9th grade. Structural equation modeling and bootstrapping were utilized to access the mediating roles of family variables and adolescents' insecurity. Two models, including the interparental conflict model and the family conflict model, were conducted separately. Findings indicated that the model fit was adequate for both models. Differential findings for each model were discussed, along with implications and contributions for understanding the relations between parental depressive symptoms and adolescents' adjustment.