Objective: To investigate a measles outbreak that spread to Japan and Taiwan, China during March–May 2018, exploring the characteristics of the super-spreading event. Methods: A contact investigation of the index case and reconstruction of the epidemiological dynamics of measles transmission were conducted. Employing a mathematical model, the effective reproduction number was estimated for each generation of cases. Results and discussion A single index case gave rise to a total of 38 secondary cases, 33 in Japan and five in Taiwan, China. Subsequent chains of transmission were observed in highly vaccinated populations in both Japan and Taiwan, China. The effective reproduction number of the second generation was >1 for both Japan and Taiwan, China. In Japan, the reproduction number was estimated to be <1 during the third generation. Vaccination of susceptible individuals is essential to prevent secondary and tertiary transmission events.