In light of the dynamic systems perspective, the current study expanded existing literature by examining the moderating effect of maternal sensitivity on the quadratic association between infant negative reactivity and future executive function development. Using a longitudinal, multimethod design, we addressed executive function development among preschoolers. This study utilized data from the Family Life Project (N = 1292). Infant negative reactivity at 6 months, maternal sensitivity across first 3 years, and executive functions during preschool age were observational assessed. A path model with moderation analyses revealed a U-shaped quadratic association between infant negative reactivity and preschoolers’ inhibitory control, only when maternal sensitivity was high. The results suggest that maternal sensitivity may assist infants with both low and high, but not moderate, levels of negative reactivity towards better executive function development. Findings support the ongoing nonlinear person-environment interplay during early years of life.