In a sample of 72 mothers with and without a history of depression and their adolescent children, maternal depression history, current maternal depressive symptoms, intrusive and withdrawn parental behavior, and adolescent caretaking behaviors were examined as predictors of adjustment in these youth. Two types of caretaking behaviors were examined: emotional (e.g., caring for a parent's emotional distress) and instrumental (e.g., looking after younger siblings). Although adolescents of mothers with and without a history of depression were comparable on levels of both types of caretaking, caretaking was associated with adolescents' reports of anxiety-depression and mothers' reports of social competence only for adolescents of mothers with a history of depression. Moreover, regression models showed that among children of mothers with a history of depression, emotional, but not instrumental, caretaking was related to adolescents' anxiety-depression symptoms and social competence after controlling for current parental depressive symptoms and stressful parenting behaviors. Theoretical and clinical implications are discussed.