The purpose of this chapter is to discuss the similarities and differences between high school applications of positive behavior support {(PBS)} and primary school settings. An increased focus on the organizational impact of size and departmental structure is discussed. Connections between academic, behavioral, social, and academic supports are highlighted. High school support has been framed under many unique labels, and the current emphasis on restructuring secondary schools has received considerable programmatic and monetary attention {(Gates} Foundation, 2003). Researchers, practitioners, and policy makers have been struggling to find new ways to address the needs of larger, highly departmentalized schools. Distinguishing promising practices with limited data from well-documented evidenced-based supports appears to become problematic as students get older and move into high school environments.