COVID-19 is the infectious disease caused by a recently discovered SARS-CoV-2. Following an initial outbreak in December 2019 in Wuhan, China, the virus has spread globally culminating in the WHO declaring a pandemic on 11 March 2020. We present the case of a patient with an initial presentation of COVID-19 pneumonitis requiring mechanical ventilation for nearly 2 weeks and total admission time of 3 weeks. She was given prophylactic dose anticoagulation according to hospital protocol during this time. Following a week at home, she was readmitted with acute massive pulmonary embolism with severe respiratory and cardiac failure, representing the first such case in the literature.