Spontaneous pneumothorax is a rare but potentially fatal complication of coronavirus infection and COVID-19 pneumonia. Data is limited to guide clinicians in the setting of spontaneous pneumothorax when conservative management fails and operative intervention is required. We report the clinical course and operative strategy for a patient who presented with sequential bilateral spontaneous pneumothorax after being diagnosed with severe COVID-19 pneumonia. Conservative management with bilateral tube thoracostomies failed to resolve persistent alveolar-pleural fistulae, and ultimately the patient recovered after synchronous bilateral VATS blebectomies in the operating room. The timing and treatment of spontaneous pneumothorax requires follow-up education and surveillance for patients with this disease, as lack of prompt treatment outside the hospital could increase patient mortality. Spontaneous pneumothorax is a concern in patients who re-present with recurrent symptoms after COVID-19 diagnosis. When conservative treatment fails, surgery can safely be performed in COVID-19 patients with simultaneous bilateral pneumothorax with full functional recovery.