Building on the conceptual framework of emotional security theory (Davies and Cummings in Psychol Bull 116:387-411, 1994), this study longitudinally examined multiple factors linking parental depressive symptoms and child internalizing symptoms. Participants were 235 children (106 boys, 129 girls) and their cohabiting parents. Assessments included mothers' and fathers' depressive symptoms when children were in kindergarten, parents' negative expressiveness when children were in first grade, children's emotional insecurity 1 year later, and children's internalizing symptoms in kindergarten and second grade. Findings revealed both mothers' and fathers' depressive symptoms were related to changes in children's internalizing symptoms as a function of parents' negative emotional expressiveness and children's emotional insecurity. In addition to these similar pathways, distinctive pathways as a function of parental gender were identified. Contributions are considered for understanding relations between parental depressive symptoms and children's development.