Many children and adolescents referred by schools for psychiatric consultation present with a highly complex clinical picture, which does not fit neatly into a classic diagnostic category. The child and adolescent psychiatrist is viewed as a leader in making both psychiatric and educational recommendations in these difficult situations. However, one is often in a dilemma, not only about the student’s diagnostic and psychiatric treatment needs, but also about how to guide the parents and school administration. Other challenges may include risk assessments for students who are making threats in school as well as the intricacies of interfacing with lawyers, educational advocates, and psychiatric emergency room staff. Using two clinically complex cases, this CCB bridges the gap between knowledge of diagnosis and treatment and the challenges of performing real-life school consultations. Each case is representative of the complex diagnostic issues as well as the evolving educational and treatment needs of these students. The importance of teasing out cognitive and language deficits is highlighted. Both cases illustrate the critical role played by the child and adolescent psychiatrist as a mediator between school officials and parents.