The growing base of research on parenting stress and its relation to child behavior problems has largely paralleled the emergence of developmental psychopathology as a field of inquiry. Specifically, the focus on mechanism rather than main effects has begun to elevate explanatory models in the connection between parenting stress and a variety of adverse child and parent conditions. Still, work on parenting stress is limited by conceptual confusion, the absence of attention to developmental differentiation, a focus on child-specific rather than system influences. Recent research on these parenting stress issues is briefly reviewed, highlighting studies that have illustrated developmental psychopathology perspectives. A conceptual model is offered to illustrate the complex recursive nature of connections between parenting stress, parenting behavior, parent well-being, and children’s adjustment, and I make a case for the adoption of a more systemic perspective to influence the next generation of developmental psychopathology research on parenting stress.