For students with disabilities, the process of school inclusion often begins with a move from segregated settings into general education classrooms. School transitions can be stressful as students adjust to a new environment. This study examines the adjustment of 133 students with and without disabilities who moved from a school that served primarily students with disabilities into 23 public schools in a large urban school district in the Midwest. These students and 111 of their teachers and other school staff rated the degree that students felt they belonged in their new schools and the quality of their social interactions. Results show that students who experienced more positive and fewer negative social interactions with school staff had higher school belonging. Teachers accurately noted whether students felt they belonged in their new settings, but were not consistently able to identify student perceptions of negative social interactions with staff. Implications for inclusion and improving our educational system are explored.