Early social withdrawal and protective parenting predict a host of negative outcomes, warranting examination of their development. Mothers' accurate anticipation of their toddlers' fearfulness may facilitate transactional relations between toddler fearful temperament and protective parenting, leading to these outcomes. Currently, we followed 93 toddlers (42 female; on average 24.76 months) and their mothers (9% underrepresented racial/ethnic backgrounds) over 3 years. We gathered laboratory observation of fearful temperament, maternal protective behavior, and maternal accuracy during toddlerhood and a multi-method assessment of children's social withdrawal and mothers' self-reported protective behavior at kindergarten entry. When mothers displayed higher accuracy, toddler fearful temperament significantly related to concurrent maternal protective behavior and indirectly predicted kindergarten social withdrawal and maternal protective behavior. These results highlight the important role of maternal accuracy in linking fearful temperament and protective parenting, which predict further social withdrawal and protection, and point to toddlerhood for efforts of prevention of anxiety-spectrum outcomes.