Objective: To conduct an exploratory investigation of possible relationships between individual levels of social anxiety and the ability to classify emotional expressions in a group of schoolchildren observing pictures of children of similar age. Method: One hundred forty-nine second- and third-grade schoolchildren underwent a facial expression discrimination trial. Children were characterized on the basis of the number of spontaneous comments they made during a pause in the trial, and on their scores on the Liebowitz Social Anxiety Scale, the Stevenson-Hinde and Glover Shyness-to-the-Unfamiliar Scale, and the Cloninger Harm Avoidance scale. The scales were filled in by appropriately trained teachers. Results: The overall rate of correct identification was 72%, without gender-associated differences. Regression analyses showed that higher rates of misidentifications were significantly associated with higher scores on the Liebowitz scale and fewer spontaneous comments. Misidentifications of the "anger" expressions (most often misclassified as "disgust") were associated with higher ratings on the Liebowitz scale when children were exposed to a boy's picture and by fewer spontaneous comments when children were exposed to a girl's picture. Misidentification of a neutral expression of a girl's picture (most often misclassified as "sadness") was significantly associated with fewer spontaneous comments. Conclusions: These pilot results suggest that a child's ability to correctly identify other children's basic emotions is partially associated with his or her level of observed social shyness.