The COVID-19 pandemic affected millions around the globe, with front line healthcare workers (HCW) amongst the most vulnerable. The Emergency Department (ED) was the first line of care for all patients infected with the virus, making HCWs in the ED one of the most exposed populations during the pandemic. We highlight the case of a 35-year-old ED physician who developed COVID-19 infections on three separate instances during the peaks of each wave despite the usage of personal protective equipment and being triple vaccinated.