The present study investigated whether salient preadolescent behaviors and experiences predicted parents' and teachers' underestimation of preadolescents' shyness. Participants included a community sample of 129 fifth and sixth graders, along with one parent and teacher per preadolescent. Preadolescents, parents, and teachers provided reports about preadolescents' shyness, and parents and teachers rated preadolescents' prosocial and aggressive behaviors, peer victimization experiences, and academic performance. Results indicated that parent- and teacher-reported prosocial behavior, teacher-reported aggressive behavior, and parent-reported peer victimization were associated with lower parent and teacher reports of preadolescent shyness, relative to preadolescent reports, controlling for demographic variables and parent stress. Additionally, higher parent-reported academic performance was associated with lower teacher reports of preadolescent shyness, compared to preadolescent reports. These findings suggest that preadolescents with higher levels of relatively conspicuous behaviors and experiences feel more shyness than their parents and teachers report.