Previous research has suggested that mothers' behaviors may serve as a mechanism in the development from toddler fearful temperament to childhood anxiety. The current study examined the maternal characteristic of accuracy in predicting toddlers' distress reactions to novelty in relation to temperament, parenting, and anxiety development. Ninety-three two-year-old toddlers and their mothers participated in the study. Maternal accuracy moderated the relation between fearful temperament and protective behavior, suggesting this bidirectional link may be more likely to occur when mothers are particularly attuned to their children's fear responses. An exploratory moderated mediation analysis supported the mechanistic role of protective parenting in the relation between early fearful temperament and later anxiety. Mediation only occurred, however, when mothers displayed high accuracy. Results are discussed within the broader literature of parental influence on fearful children's development.