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During the second wave of COVID-19, a number of patients requiring invasive or noninvasive pressure support ventilation rose significantly. The cases of pneumomediastinum (PM), pneumothorax (PTX), and subcutaneous emphysema (SCE) were also reported, largely attributed to barotrauma with observation of some spontaneous cases. Here, we present seven moderate-to-severe COVID-19 cases with variable severity developing PM with or without PTX and SCE during the course of hospitalization. Five received noninvasive ventilation, of whom two required invasive mechanical ventilation. The remaining two patients received oxygen therapy alone. Two patients required insertion of intercostal chest drainage tubes for pneumothoraces. Appropriate medical management was given to all patients. Three patients improved and were discharged from the hospital, while four expired. The case series highlights need of early diagnosis, constant monitoring, and judicious use of pressure support ventilation to prevent air leak complications in COVID-19 patients in order to improve their prognostic outcomes.