The link between parental depressive history and parenting styles is well established, as is the association of parenting with child psychopathology. However, little research has examined whether a depressive history in one parent predicts the parenting style of the other parent. As well, relatively little research has tested transactional models of the parenting-child psychopathology relationship in the context of parents' depressive histories. In this study, mothers and fathers of 392 children were assessed for a lifetime history of major depression when their children were 3 years old. They then completed measures of permissiveness and authoritarianism and their child's internalizing and externalizing symptoms when children were 3, 6, and 9 years old. The results showed that a depressive history in one parent predicted the other parent's permissiveness. Analyses then showed that child externalizing symptoms at age 3 predicted maternal permissiveness and authoritarianism and paternal permissiveness at age 6. Maternal permissiveness at age 6 predicted child externalizing symptoms at age 9. No relationships in either direction were found between parenting styles and child internalizing symptoms. The results highlight the importance of considering both parents' depressive histories when understanding parenting styles, and support transactional models of parenting styles and child externalizing symptoms.