An elderly man with COPD and heart failure was admitted to the Family Medicine Inpatient Service from the Emergency Department (ED) after experiencing acute onset of shortness of breath at home. He had recently been briefly hospitalized with COVID pneumonia. Upon arrival in the ED, he was requiring continuous positive airway pressure to maintain oxygen saturations. Overall, physical exam was notable for mild respiratory distress. Lab evaluation was unremarkable, but chest x-ray showed a right sided pneumothorax. Spontaneous pneumothoraces have been described in post-COVID cases, with COPD and mechanical ventilation thought to be risk factors. Treatment consists of supportive cares, needle decompression and thoracostomy if necessary. Providers should be aware of this rare albeit serious complication and monitor higher risk patients appropriately.