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This study examined whether the trajectory of depressive symptoms mediated the relation between parent-adolescent relationship quality during adolescence and parenting stress 24 years later. Data were obtained from the public use of The National Longitudinal Study of Adolescent to Adult Health (Add Health). Findings indicated that perceived parent-adolescent relationship quality during adolescence was related to parenting stress when participants become parents to their own children 24 years later for both mothers and fathers. The intergenerational transmission of parenting was mediated by the depressive symptoms slope in the father model but not in the mother model. Results highlight the potential long-term value, in terms of adult emotional health and parenting stress, of interventions designed to enhance parent-adolescent relationship quality during adolescence.