Consistently, research has shown that higher levels of maternal education are linked to positive child outcomes; however, few studies have examined whether increases in maternal education after the child is born are a protective or a risk factor for child outcomes. Given a large minority of mothers complete education after having children, understanding the impact of maternal increases in education may be important. We aimed to examine the association between increases in maternal education during the first five years of the child’s life and later child outcomes and explore the mediating role of the home learning environment and positive parenting. Further, we examined the moderating role of baseline education in the association between increases in maternal education and parenting behaviors. Data from the Fragile Families and Child Wellbeing Study (FFCWS), a longitudinal birth cohort study comprising 4898 families, were used. Using structural equation modeling, findings indicated that increases in maternal education were significantly associated with greater child academic skill at age nine (b = 0.04) but not with child externalizing behavior. Increases in maternal education were not linked to home learning environment or positive parenting at age five; however, higher levels of positive parenting and a better-quality home learning environment were associated with more optimal child outcomes. Baseline maternal education did not moderate the association between increases in maternal education and home learning environment and positive parenting. Models accounted for associations with several demographic covariates, including maternal intellectual ability, child effects on parenting behaviors, and continuity of child outcomes. Findings provide limited support for policies that offer support for mothers to complete educational programs that may subsequently foster child academic skills.