Parenting beliefs have a significant impact on the way parents interact with their children, but little is known about how children’s behaviors may relate to changes in parents’ childrearing beliefs over time, and whether changes in parents’ beliefs may mediate the relation between child behavior and changes in parenting practices. We examined whether child externalizing behaviors at first grade related to changes in mothers’ and fathers’ obedience-oriented childrearing beliefs between first and fourth grade; whether parent anxiety interacted with child behavior problems to create conditions under which parents’ beliefs were more resistant to change; and how changes in beliefs, in turn, related to changes in parents’ autonomy granting behaviors between first and fifth grade. Participants included 895 families enrolled in a rich archival dataset, the NICHD Study of Early Childcare and Youth Development. Results showed that greater child externalizing behavior at first grade related to decreases in autonomy granting behaviors among mothers and high-anxiety fathers, as well as increases in low-anxiety mothers’ traditional parenting beliefs. Mothers’ more traditional beliefs related to declines in their own autonomy granting, and fathers’ more traditional beliefs related to declines in their own and their partner’s autonomy granting. Finally, a significant indirect effect showed that for mothers low in anxiety, child externalizing behaviors related to increases in traditional parenting beliefs which, in turn, related to decreases in mothers’ autonomy granting. Findings are discussed in terms of parent gender differences and psychological flexibility.