In this study, the relation between self-reported parental personality, using the five-factor model, and observed parenting was examined. In addition, we investigated the moderating role of observed preschoolers’ temperamental effortful control (i.e., the ability to suppress a dominant response in order to perform a subdominant response) in this relation. The sample included 89 two-parent families and their firstborn 36-month-old children. Weak to modest associations were found between personality and observed parenting. Effortful control appeared to moderate the relation between parental personality and parenting: fathers’ neuroticism was positively associated with fathers’ positive control and fathers’ extraversion was positively associated with fathers’ negative control, but only when children had a low level of effortful control. Thus, individual differences in personality appeared to be most relevant during the demanding experience of parenting a less self-regulated child.