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Toddlers who are shy may be at risk for poor peer relations, social withdrawal, and social anxiety. A large body of literature supports that parenting behaviors may mitigate this risk, however findings are seemingly mixed regarding whether high warmth parenting and encouraging parenting facilitate or hinder children's social behaviors. The present study employed an experimental design to determine the specific influence of high warmth maternal parenting and encouragement of independence maternal parenting on shy toddlers' approach and avoidance behaviors in a play session with unfamiliar peers. One hundred and nineteen mothers of toddlers between 21 and 27 months of age completed temperament and other questionnaires. The toddlers were classified as shy or non-shy based on mothers' responses on a social fear subscale of the temperament questionnaire. One shy and two non-shy toddlers and their mothers participated in each of a total of 32 25-minute play session, during which time shy toddlers' mothers' behaviors were manipulated and children's approach and avoidance behaviors were recorded for later coding. Results indicated that shy toddlers demonstrated less approach and more avoidance during the initial baseline of the study. However, shy toddlers did not increase their approach or decrease their avoidance following either manipulation. Exploratory analyses provide some support for the beneficial impact of encouragement of independence parenting; shy children were indistinguishable from their non-shy peers in their avoidance behaviors after the encouragement of independence intervention, but not after the high warmth intervention. Despite the limited findings in the present study, the broader literature base suggests that the maternal high warmth and encouragement of independence behaviors that were the focus of the present study have the potential to teach shy toddlers to approach instead of avoid social novelty and merit further study.