Schoolwide positive behavior interventions and supports (SWPBIS) are an increasingly popular framework for school improvement practices, but many high schools are still lagging behind their elementary counterparts. High school leadership teams can struggle with merging the SWPBIS framework with current operations, and there are limited examples of how schools have overcome the challenges. Implementation does not happen all at once but in stages marked by specific activities. Through a series of case examples, this article details the stages, challenges, and corresponding strategies that eight high schools used to improve implementation of the SWPBIS framework.