This study was a prospective 2-year longitudinal investigation of associations between negative maternal parenting and disruptive child behavior across the preschool to school transition. Our main goals were to 1) determine the direction of association between early maternal negativity and child disruptive behaviors across this important developmental transition and 2) examine whether there would be different patterns of associations for boys and girls. Participants were 235 children (111 girls; T1; M = 37.7 months, T2; M = 63.4 months) and their mothers and teachers. Observational and multi-informant ratings of child disruptive behavior showed differential patterns of stability and associations with measures of parenting risk. Results indicated bidirectional and interactive contributions of externalizing behavior and negative parenting across time. Results also indicated that risk mechanisms operate similarly for both sexes. Findings support transactional models of disruptive child behavior that highlight the joint contributions of parents and children.