This study examined bidirectional associations between mothers' depressive symptoms and children's externalizing behavior and whether they were moderated by preschool-age effortful control and gender. Mothers and teachers reported on 224 primarily White, middle-class children at ages 3, 5, and 10. Effortful control was assessed via behavioral battery and mother ratings. Structural equation modeling indicated that maternal depressive symptoms at child age 3 predicted more externalizing behavior at age 10 among children with low effortful control and among boys. Externalizing behavior at age 3 predicted fewer depressive symptoms at the age 10 assessments among mothers of children with high effortful control. Boys with suboptimal self-regulation exposed to high levels of maternal depressive symptoms were at greatest risk for school-age behavioral problems.