Background: Despite recent tobacco control efforts, adolescent vaping remains an epidemic in the United States. The purpose of our study was to understand high school student vaping behaviors using the perceptions of Massachusetts school personnel during the critical window from when the Massachusetts statewide flavor ban legislation was passed in November 2019 through the first year of the COVID-19 pandemic. Methods: High school personnel throughout Massachusetts were invited to complete a cross-sectional survey. Analysis of survey responses was conducted in R. Results: A total of 162 respondents completed the survey representing 137 schools that draw enrollments from 216 (61%) of the 352 cities and towns in Massachusetts. The most popular products that respondents believed their students were using were JUULs (95.7%), other e-cigarettes (85.3%), and disposable vapes (79.6%). Following the flavor ban, the majority (90.7%) did not report an increase in combusted tobacco product use. All participants (100%) reported wanting more access to prevention and treatment resources. Conclusions: Our findings suggest that a comprehensive flavor ban may be an effective tobacco control policy that does not appear to promote student switching from vaping products to combusted tobacco products. These data also indicate that schools report needing additional resources to address the vaping epidemic.