Menthol cigarettes have had a profound adverse effect on public health. On 1 June 2020, Massachusetts became the first state to ban the sale of menthol cigarettes. We explored how perceptions of the ban and smoking behaviors changed over time among a group of 27 individuals who smoked menthol cigarettes at our safety-net hospital. In a convergent mixed methods study, we administered questionnaires and interviews simultaneously at two timepoints: 1 month pre-ban and 6 months post-ban. Pre-ban, we assessed perceptions of the ban and anticipated smoking behaviors after the ban. Post-ban, we assessed participants’ actual smoking behaviors and elicited suggestions to avoid unintended consequences that might undermine intended policy effects. Several respondents perceived the Massachusetts ban as positive because it could promote smoking cessation, prevent youth initiation, and mitigate unfair targeting of socioeconomically disadvantaged populations. Others perceived the ban as an overreach of government policy, financially motivated, and unfairly targeting the Black community. Many continued to smoke menthol cigarettes obtained outside Massachusetts. Individuals suggested promoting tobacco treatment for people affected by the ban and a national ban to circumvent out-of-state purchasing of menthol cigarettes. Our findings suggest that in order to be most effective, healthcare systems must promote tobacco treatment and ensure that treatment is accessible to all individuals affected by the ban.