We examined the indirect relations between maternal parenting stress when children were 15months of age and children's vocabulary and academic skills when they were about to enter kindergarten, testing for potential mediation by mother-child closeness and children's self-regulation skills. Participants had been involved in the Early Head Start Research and Evaluation Project and included 1760 European American, African American, and Hispanic low-income mother-child dyads. Structural equation modeling revealed that mothers' parenting stress when children were 15 months old was inversely related to children's vocabulary and academic skills just prior to kindergarten, and that mother-child closeness at 25 months and children's pre-kindergarten self-regulation skills consecutively mediated these associations in a three-path mediation model. The findings highlight the benefits of mother-child closeness in toddlerhood, and negative implications of maternal parenting stress. The discussion focuses on how maternal parenting stress is related to later maternal behavior, ultimately shaping child outcomes. (author abstract)