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Objective: The coronavirus disease 2019 (COVID-19) pandemic reached New York City in March 2020, leading to a state of emergency that affected many lives. Patients who contracted the disease presented with different phenotypes. Multiple reports have described the findings of computed tomography scans of these patients, several with pneumothoraces, pneumomediastinum, and subcutaneous emphysema. Our aim was to describe the incidence and management of pneumothorax, pneumomediastinum, and subcutaneous emphysema related to COVID-19 found on radiologic imaging. Methods: A retrospective chart review was conducted of all confirmed COVID-19 patients admitted between early March and mid-May to two hospitals in New York City. Patient demographics, radiological imaging, and clinical courses were documented. Results: Between early March and mid-May, a total of 1866 patients were diagnosed with COVID-19 in the two hospitals included in the study, of which 386 were intubated. The majority of these patients were men (1090, 58.4%). The distribution of comorbidities included the following: hypertension (1006, 53.9%), diabetes (544, 29.6%), and underlying lung disease (376, 20.6%). Among the 386 intubated patients, 65 developed study-specific complications, for an overall incidence of 16.8%; 36 developed a pneumothorax, 2 developed pneumomediastinum, 1 had subcutaneous emphysema, and 26 had a combination of both. The mean time of invasive ventilation was 14 days (0–46, interquartile range = 6–19, median 11). The average of highest positive end expiratory pressure within 72 h of study complication was 11 (5–24) cmH 2 0. The average of the highest peak inspiratory pressure within 72 h of complication was 35.3 (17–52) cmH 2 O. In non-Intubated patients, 9/1480 had spontaneous pneumothorax, for an overall incidence of 0.61 %. Conclusion: Intubated patients with COVID-19 pneumonia are at high risk of pneumothorax, pneumomediastinum, and subcutaneous emphysema. These should be considered in differential diagnosis of shortness of breath or hypoxia in a patient with a new diagnosis of COVID-19 or worsening hemodynamics or respiratory failure in an intensive care unit setting.