The number of schools implementing school-wide positive behavior support (SWPBS) practices nationwide is increasing, but still little is known about the fidelity with which teachers implement SWPBS practices in the classroom. Specifically, data are needed that reflect the consistency with which classroom-based SWPBS practices are implemented, as well as challenges to implementation faced by school personnel, to ensure the best possible behavioral and academic outcomes for students. In this study, personnel in Connecticut schools implementing SWPBS (N = 171) were surveyed, and results indicate that although classroom-based SWPBS practices are implemented very consistently by the majority of respondents, certain practices are somewhat challenging to implement. Implications for improving practice and training are offered.