Shy children are wary in the face of new social situations and perceived social evaluation. In this regard, the transition to kindergarten may represent a particularly challenging task for shy children. In this review, we explore the kindergarten classroom as a particularly stressful context for shy children. We examine the adjustment difficulties that shy children may face when starting school, including problems with peers, teachers, and academics. We also consider what teachers can do to help ease the school adjustment problems of shy children. It is our hope to continue to raise awareness in parents, educators, and mental health care professionals with regards to the challenges that shy children face at school.