Schoolwide Positive Behavioral Intervention and Supports (SWPBIS) is a framework for establishing a schoolwide positive social culture with a continuum of behavior supports and an effective learning environment for all students. This framework was initially implemented in elementary and middle schools and more recently in high schools. Coaches for high schools implementing SWPBIS often comment on how implementation looks different in high schools and takes longer. This article explores how the high school context (i.e., size of school and organizational culture, developmental age of students) impacts the foundational systems of the SWPBIS framework (i.e., leadership system, communication system, data system) and how coaches and others can take this into consideration when supporting high schools in implementation.