Background: Obesity is a complex health problem affecting more than one-third of school-aged youth. The increasing obesity rates in Kansas and Missouri has been particularly concerning, with efforts being made to improve student health through the implementation of school wellness policies (SWPs). The primary purpose of this study was to conduct a rigorous assessment of SWPs in the bi-state region. Methods: SWPs were collected from 46 school districts. The Wellness School Assessment Tool (WellSAT) was used to assess comprehensiveness and strength. Additionally, focus group discussions and an online survey were conducted with school personnel to identify barriers and supports needed. Results: Assessment of the SWPs indicated that most school districts failed to provide strong and specific language. Due to these deficiencies, districts reported lack of enforcement of policies. Several barriers to implementing the policies were reported by school personnel; supports needed for effective implementation were identified. Conclusions: To promote a healthful school environment, significant improvements are warranted in the strength and comprehensiveness of the SWPs. The focus group discussions provided insight as to where we need to bridge the gap between the current state of policies and the desired beneficial practices to support a healthy school environment.