In response to the COVID-19 outbreak, the South Korean government mandated that all universities and schools deliver courses online to minimize transmission of the virus. In order to provide insight into the experiences of those implementing this sudden and drastic shift to online teaching, the vignettes of three educators are presented. Examination of these cases revealed three key themes. First, teachers should provide at least some portion of their class online at all times as a contingency plan for disasters necessitating fully online course delivery. Second, technology-enhanced communication experiences can enhance faculty members’ online teaching ability and self-efficacy. Third, educational administrators also bear responsibility in enhancing the preparedness of institutions for the transition to online teaching in response to a disaster. The paper concludes with suggestions on how teachers and administrators can increase their preparedness for disasters like COVID-19 through the use of and support for online teaching.