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This study examines potential mechanisms linking maternal depressive symptoms over 2 years postpartum with child behavior problems at school-age in a sample of adolescent mothers and their first-born child. Potential mechanisms include: mother-reported caregiving engagement at 6 months; observed parental nurturance and control, and child competence and affect at 24 months; and mother-reported resilience at 7 years based on achievement of adult developmental tasks. One hundred eighteen low-income African American adolescent mothers were recruited at delivery and followed through child age 7 years. Maternal depressive symptom trajectories over 24 months were estimated (low, medium, and high) based on mother-reported depressive symptoms. Direct and indirect associations between depressive symptom trajectories with 7-year maternal depressive symptoms and child behavior problems were examined. The high maternal depressive symptom trajectory was associated with 7-year maternal depressive symptoms (b = 5.52, SE = 1.65, p < .01) and child internalizing problems (b = 7.60, SE = 3.12, p = .02) and externalizing problems (b = 6.23, SE = 3.22, p = .05). Caregiving engagement among high depressive symptom trajectory mothers was significantly associated with observed child affect (b = −0.21, SE = 0.11, p = 0.05). Parental nurturance in toddlerhood mediated the association between high maternal depressive symptom trajectory and child internalizing problems at 7 years (indirect effect b = 2.33, 95% CI: 0.32–5.88). Findings suggest that family based interventions to promote parenting and adolescent resiliency strengthening may be beneficial in this population.