Shyness in childhood has been linked to multiple adjustment outcomes, including poor peer relations, internalizing problems, and clinical anxiety. However, shyness does not consistently emerge as a negative predictor of children's success. This incongruity may stem, in part, from variations in the operationalization and measurement of shyness in different studies. Researchers often combine parent and teacher ratings of shyness, but correlations between parent and teacher reports are consistently small to medium. The purpose of this study is to examine parent and teacher ratings of shyness as they predict language and attention skills in preschool children, and explore discrepancies between parent and teacher ratings of shyness. Participants were 104 preschool children (48 males, 56 females), enrolled in 22 classrooms. Results from multi-level modeling revealed that teacher, but not parent, ratings of shyness using the shyness subscale of the Children's Behavior Questionnaire (CBQ) were significantly and negatively associated with children's early language and attention skills. Follow-up exploratory factor analyses with parent and teacher CBQ shyness subscale ratings revealed a similar two-factor structure reflecting shyness and low sociability. Results suggest that a) discrepancies between parents' and teachers' views of children's shy behaviors may stem from the different contexts and developmental time periods in which they observe children, and b) teachers' ratings of shyness are more closely associated with children's skills in an academic setting. Implications for research are discussed. (author abstract)