Renewed federal requirements for local school wellness policies highlighted the continued importance of supporting school districts as they implement and evaluate wellness initiatives. Superintendents—as school district leaders—play a critical role in wellness policy implementation and evaluation; however, to our knowledge, no studies examine their perspectives or experiences with the most recent federal rule or wellness initiatives more broadly. This study qualitatively examined superintendents’ perspectives, experiences, and recommendations with wellness policy implementation and evaluation. Focus groups (n = 39) and follow-up interviews (n = 14 of the focus group participants) were conducted with superintendents from March to July 2017. Coders organized and coded transcript data using Atlas.ti, Version 8 to facilitate thematic analysis. Superintendents had overall positive perceptions of wellness policies and reported that implementation improved over time. Most described wellness approaches beyond typical wellness policy domains, including social-emotional learning and staff wellness. Evaluation of wellness policies was noted to be a challenge, and superintendents requested more tools and resources, as well as opportunities to learn from “best practices.” Increased local and state accountability were recommended to facilitate motivation for other superintendents to engage with wellness. This study adds to the literature on a critical stakeholder in the school wellness field. Advocates and technical assistance providers can apply superintendents’ recommendations to engage more district leaders in these initiatives.