Background: The topic of natural immunity related to severe acute respiratory syndrome coronavirus 2 remains controversial. Although evidence suggests postinfection immunity can be achieved, there have been reported cases of reinfection with similar or milder symptoms. Information on severe disease manifestation during reinfection is not known. We present a case of reinfection with a more severe presentation as compared with the initial infection. Case Report: We describe a white male patient from a nursing home who was reinfected with severe acute respiratory syndrome coronavirus 2 with severe disease manifesting as dyspnea, fevers, and encephalopathy with hypoxemic respiratory failure requiring intubation, elevated inflammatory markers, and lung infiltrates on imaging, after initially testing positive with mild symptoms 2 months prior to presentation. Notably, severe acute respiratory syndrome coronavirus 2 antibodies were detected, which indicated this was a coronavirus disease 2019 reinfection. After treatment with remdesivir, dexamethasone, and convalescent plasma, he was subsequently extubated and discharged home after 2 weeks. Conclusion: It is not clear whether an initial infection with severe acute respiratory syndrome coronavirus 2 and recovery provides prolonged immunity beyond 2 months. Furthermore, even if antibodies are present, it does not guarantee an attenuated course during reinfection. Therefore, vaccination plays an important role in prevention. Long-term cohort studies will be needed to study the factors behind reinfection.