Consistent with models of environmental sensitivity (Pluess, 2015), research suggests that the effects of parents’ behaviors on child adjustment are stronger among children who struggle to regulate their thoughts, feelings, and behaviors compared with children with better self-regulation. This study extended prior research by assessing maternal representations of the child, which presumably underlie mothers’ parenting behaviors, to evaluate the moderating influence of preschoolers’ self-regulation on relations between mothers’ representations and changes in children’s negative and positive developmental adjustment outcomes from preschool to first grade. Participants were 187 mothers and their preschoolers. Mothers’ representations were assessed via the coherence of their verbal narratives regarding their preschooler and teachers reported on preschoolers’ self-regulation. In preschool and first grade, examiners rated children’s externalizing behavior problems and ego-resilience, and teachers rated children’s externalizing behavior problems and peer acceptance. Consistent with the environmental sensitivity framework, the coherence of mothers’ narratives predicted changes in adjustment among children with self-regulation difficulties, but not among children with better self-regulation. Preschoolers with self-regulation difficulties whose mothers produced incoherent narratives showed increased externalizing behavior problems, decreased ego-resilience, and lower peer acceptance across the transition to school. In contrast, preschoolers with better self-regulation did not evidence such effects when their mothers produced incoherent narratives. The implications of these findings for understanding and supporting children’s adjustment during the early school years are discussed.