The goal of this study was to explore the moderating role of maternal personality and parenting characteristics in the links between shyness and adjustment in kindergarten. Participants were 197 children enrolled in kindergarten programs (and their mothers and teachers). Multisource assessment was employed, including maternal ratings, behavioral observations, teacher ratings, and individual child interviews. Results indicated that shyness was associated with a wide range of socio-emotional and school adjustment difficulties in kindergarten. Moreover, support for the moderating role of parenting was also found. Relations between shyness and certain indices of maladjustment were stronger among children with mothers characterized by higher neuroticism, BIS sensitivity, and an overprotective parenting style, and weaker for mothers characterized by high agreeableness and an authoritative parenting style.