The goal of this work was to examine the complex interrelation of mothers’ early gentle control and sensitivity in predicting children’s effortful control (EC) and academic functioning. Maternal gentle control, maternal sensitivity, and children’s EC were measured when children were 18, 30, and 42 months of age (T1, T2, and T3, respectively), and measures of children’s academic functioning were combined across 72 and 84 months (T5/T6; Ns = 255, 222, 200, 162, and 143). Using structural equation modeling, results demonstrated that T1 maternal sensitivity moderated the relation between T1 maternal gentle control and T2 EC, and T3 EC predicted children’s later academic functioning. There was evidence for moderated mediation, such that when maternal sensitivity was high, children’s EC mediated the relation between T1 maternal gentle control and children’s academic functioning, even after controlling for stability of the constructs. The relation between maternal gentle control and children’s EC was not significant under conditions of low maternal sensitivity. Implications for parenting programs are offered and future research directions are discussed.