In the early 21st century, school leaders play an important role—mediating between political ambitions and policies on the one hand and local conditions in schools and classrooms on the other. Mediating between general policies and local needs and constraints becomes increasingly challenging in diverse and complex societies. One interesting element of this dilemma is how to handle the balance between inclusion and segregation of children who have difficulties following mainstream teaching. In such cases, educational policies have to be interpreted in the context of the needs and prospects of specific individuals; that is, school leaders have to close the gap between the general (policy) and the specific (students and their capacities). When engaging in such decisions, school leaders as mediators rely on categories that characterize students and their abilities. In recent decades, neuropsychiatric categories, especially attention deficit/hyperactivity disorder (ADHD) and attention deficit disorder (ADD), have played an increasingly prominent role when such decisions are made, and this is an international phenomenon. An interesting set of problems that has not been the focus of much research is how school leaders perceive such dilemmas of deciding on the educational futures of children. In addition, we know little about what happens when children, after being diagnosed with ADHD, are placed in special educational groups. Important issues at this level concern what the teaching and learning situation they encounter is like, and what the likelihood is that participation in such special educational groups will improve their opportunities for the future. In other words, what are the gains and losses of such placements for students, and does the placement in a special educational group contribute to a successful educational career? Swedish school leaders emphasize the dilemmas they perceive in such high-stakes situations when the diagnosis ADHD is invoked as the main explanation for learning difficulties, since the most frequent outcome is segregation and placement in a special teaching group. In addition, research shows that the instructional strategies dominating these segregated settings are highly individualized forms of teaching, where often one teacher is instructing one student. Despite this arrangement, it is found that the students do not actively contribute to the instructional activities and dialogues; rather, it is the teacher who dominates the instruction. The question raised is whether exposure to such special educational practices will prepare children for a return to their regular classroom. If this is not the case, the dilemma is that the educational solution offered risks being counterproductive in the sense that the student will be even further away from reintegration into mainstream classrooms.