This article proposes a family system approach to improve our understanding on family stress processes. Examining effects within (actor) and between (partner) parents, we explored family-based pathways through which financial stress is associated with adolescent externalizing problem behavior. Data from 340 families were analyzed, with both parents rating their financial stress and parenting stress, and parents as well as adolescents rating the parent–child communication and adolescent problem behavior. The results revealed that the association between financial stress and adolescent externalizing problem behaviors was mediated by parenting stress and parent–child communication. Although our results provided evidence for both actor and partner effects, actor effects were more prominent. No parent gender differences were found in the strength of the pathways.