ABSTRACT Building on prior cross-sectional work, this longitudinal study evaluated the proposition that maternal and paternal overreactive and authoritative parenting mediates the effect of child personality characteristics on externalizing behavior. Data from the Flemish Study on Parenting, Personality, and Problem Behavior were used in a moderated mediation analysis (N=434). Teachers rated children's Big Five characteristics, fathers and mothers rated their parenting, and 3 years later, children rated their externalizing behavior. Mediational analysis revealed both direct and indirect effects. Higher levels of Extraversion and lower levels of Benevolence were related directly to higher levels of child externalizing behavior. Higher levels of paternal authoritative parenting and lower levels of maternal overreactivity were related to lower scores on externalizing behavior. In addition, the relation between Benevolence, Emotional Stability, and externalizing behavior was partially mediated by parental overreactivity. Conscientiousness had an indirect effect on externalizing behavior through paternal authoritative parenting. Relations were not moderated by child gender. This study is of theoretical interest because the results demonstrate that parenting is a mediating mechanism that accounts for associations between personality and externalizing behavior.