The moderating effect of maternal behavior in the relations between social reticence and shyness in preschool and subsequent social withdrawal was investigated. Eighty children (47 females) were judged for degree of social reticence during play with unfamiliar peers at the age of four and mothers completed the Colorado child temperament inventory (CCTI). At the age of seven, the children were coded for degree of social withdrawal during peer play and mothers and children were observed during structured and unstructured activities. Two significant interaction effects indicated that maternal report of shyness was a positive predictor of age-seven social withdrawal when mothers lacked positivity; whereas observed social reticence was associated with higher degrees of social withdrawal when mothers were highly negative. Maternal positivity and negativity differentially influenced the development of social withdrawal in childhood, such that maternal negativity is associated with poor social functioning in children who have an established history of social withdrawal; whereas maternal positivity is associated with better social outcome for preschoolers who are viewed as temperamentally shy.