The goals of this study were to examine: (a) bidirectional associations between maternal parenting (physical punishment and guilt induction) and Chinese American preschool children’s psychosocial adjustment and (b) the role of maternal cultural orientation and child temperament in moderating parenting effects. Participants were Chinese American mothers and children (N = 163, Mage = 4.56, 53% boys). Mothers reported on their parenting practices at both Wave 1 (W1) and Wave 2 (W2) and their cultural orientations and children’s inhibitory control at W1. Teachers rated children’s prosocial, internalizing, and externalizing behaviors at both W1 and W2. A Bayesian approach to path analysis was utilized to investigate how parenting, child inhibitory control, and maternal cultural orientations work together to predict the development of children’s prosociality and psychosocial problems. Results showed that for Chinese immigrant mothers who were highly acculturated toward the American culture and for children with low levels of inhibitory control, maternal use of physical punishment predicted more externalizing problems in children. Child inhibitory control and maternal enculturation were directly associated with less W2 child internalizing and externalizing behaviors. Moreover, physical punishment predicted more internalizing behavior, whereas guilt induction predicted less child internalizing behavior. Maternal guilt induction also prospectively predicted more prosocial behavior but only for children with low levels of inhibitory control. Finally, only one child effect was significant: More W1 internalizing behavior predicted less W2 physical punishment. These effects held after controlling for temporal stabilities of the constructs and demographic covariates. Findings are discussed within the cultural context of the study.