Parenting x Child Personality interactions in predicting child externalizing and internalizing behavior were investigated in a variable-centered study and a person-centered study. The variable-centered study used data from a 3-year longitudinal study of 600 children 7 to 15 years old at Time 1 and 512 children 10 to 18 years old at Time 2. Parents rated child personality (five factor model), negative control, positive parenting, and child problem behavior, whereas children rated parental behavior. Hierarchical moderated regression analyses showed significant Parenting x Child Personality (benevolence and conscientiousness) interactions, principally for externalizing behavior. The interactions were largely replicable across informants and across time. The person-centered study, which classified participants into 3 types, showed that negative parental control was more related to externalizing behavior for undercontrollers than for resilients. Negative parental control enhanced internalizing behavior for overcontrollers.