We examined self-reported maternal and paternal harsh parenting (HP) and its effect on the moment-to-moment dynamic coupling of maternal autonomy support and children’s positive, autonomous behavior. This positive behavior coupling was measured via hidden Markov models as the likelihood of transitions into specific positive dyadic states in real time. We also examined whether positive behavior coupling, in turn, predicted later HP and child behavior problems. Children (N = 96; age = 3.5 years at Time 1) and mothers completed structured clean-up and puzzle tasks in the laboratory. Mothers’ and fathers’ HP was associated with children’s being less likely to respond positively to maternal autonomy support; mothers’ HP was also associated with mothers’ being less likely to respond positively to children’s autonomous behavior. When mothers responded to children’s autonomous behavior with greater autonomy support, children showed fewer externalizing and internalizing problems over time and mothers showed less HP over time. These results were unique to the dynamic coupling of maternal autonomy support and children’s autonomous behavior: The overall amount of these positive behaviors did not similarly predict reduced problems. Findings suggest that HP in the family system compromises the coregulation of positive behavior between mother and child and that improving mothers’ and children’s abilities to respond optimally to one another’s autonomy-supportive behaviors may reduce HP and child behavior problems over time.