SWPBIS create an environment within the school that prevents problem behaviors via promotion of prosocial and learning behaviors. External SWPBIS coaches guide schools to engage in ongoing progress monitoring and action planning to direct efforts and facilitate accurate implementation of the key SWPBIS features. The effectiveness of providing evidence-based recommendations in a systematic format via external coaching to improve schools’ fidelity of implementation of the key features of SWPBIS was evaluated as a means for coaching a large number of schools within a system. The current study found that the PBIS evaluations have mixed reliability results but lacked concurrent validity. Evaluation results revealed that a large urban school system can implement SWPBIS with fidelity. Additionally, an external coaching procedure improved the results of one of the evaluations. Urban school systems should support sustainment of SWPBIS efforts to promote appropriate behaviors. External coaches should approach working with school systems in a systematic method to improve the schools’ effective implementation of SWPBIS.