Abstract Objective: This study explored the barriers and facilitators of mask-wearing behaviors during the pandemic in Taiwan, the United States, the Netherlands, and Haiti. Methods: Face-to-face interviews were conducted in Taiwan and online interviews were conducted with participants in the United States, the Netherlands, and Haiti. Results: In general, the habit of wearing a mask before coronavirus disease 2019 (COVID-19) was reported by Taiwanese participants. Additionally, Taiwanese participants perceived that wearing a mask was a social responsibility during the pandemic, suggesting that the collectivistic context might influence mask-wearing behavior. Unlike the Taiwanese population, some people in the United States and the Netherlands were reluctant to wear masks due to perceived restrictions on their freedom. Participants from Haiti mentioned that people who wore masks encountered violence, bullying, and discrimination. The results of this study suggest that political leadership and mask mandates have a strong impact on people’s mask-wearing behavior. Conclusions: These findings have valuable implications for the design of diverse behavioral interventions to enhance mask-wearing as part of infectious disease preparedness. Additionally, the findings from these countries offer valuable insights for the development of effective public health interventions to enhance society’s resilience during the current pandemic and future infectious disease outbreaks.