Objectives: The school environment has been the focus of many health initiatives over the years as a means to address the childhood obesity crisis. The availability of low-nutrient, high-calorie foods and beverages to students via vending machines further exacerbates the issue of childhood obesity. However, a healthy overhaul of vending machines may also affect revenue on which schools have come to depend. This article describes the experience of one school district in changing the school environment, and the resulting impact on food and beverage vending machines. Study design: Observational study in Ann Arbor public schools. Methods: The contents and locations of vending machines were identified in 2003 and surveyed repeatedly in 2007. Overall revenues were also documented during this time period. Results: Changes were observed in the contents of both food and beverage vending machines. Revenue in the form of commissions to the contracted companies and the school district decreased. Conclusions: Local and national wellness policy changes may have financial ramifications for school districts. In order to facilitate and sustain school environment change, all stakeholders, including teachers, administrators, students and healthcare providers, should collaborate and communicate on policy implementation, recognizing that change can have negative financial consequences as well as positive, healthier outcomes. © 2012 The Royal Society for Public Health.