Teachers in the US are now considered integral to promoting students' mental health; here we report on two major challenges for educators in high achieving schools (HAS). The first involves high adjustment disturbances among students. We present data on nine HAS cohorts showing elevated rates of clinically significant symptoms relative to norms; rates of anxious-depressed symptoms, in particular, were six to seven times those in national norms on average. As high achieving youth often keep internalizing symptoms hidden, their teachers will need help in understanding how to identify early signs of these types of distress, and to ensure appropriate, timely interventions. The second challenge we consider has to do with relationships between service providers and parents. Data obtained from the former showed that they tend to perceive relatively wealthy parents more negatively, and as more likely to threaten litigation, compared to parents from middle- or low-income backgrounds. We discuss the importance of proactively addressing such potentially adversarial relationships for the success of both the early detection of HAS students' adjustment problems, and appropriate interventions for them. Next, we appraise how the aforementioned challenges can greatly exacerbate risks for burnout among educators in HAS settings, and how this might be alleviated via evidence-based, institutional-level interventions. Schools must ensure ongoing support for educators who carry the weighty, dual charge of tending to the emotional needs of a group of highly stressed students, in addition to ensuring their continued, exemplary levels of educational accomplishments.