Pulmonary barotrauma such as pneumothorax (PTX) is a known complication of invasive mechanical ventilation. However, it is uncommonly reported with the use of noninvasive positive pressure ventilation (NPPV) and CPAP (continuous positive airway pressure) therapy. We present a case of a 66-year-old female who presented with chronic dyspnea on exertion secondary to right-sided diaphragmatic hernia. The patient also underwent a home sleep study which suggested obstructive sleep apnea (OSA) for which she was initiated on CPAP. She then underwent surgical repair of her right diaphragmatic hernia. The patient developed pneumothorax three times over the course of the following several months, once on the right side and twice on the left side. The patient's incidences of PTX had a temporal association with the CPAP initiation. Her CPAP therapy was discontinued permanently after the third occurrence of PTX. With this case report, we highlight the risk of barotrauma with the use of CPAP for OSA. There are very few reported cases of PTX in association with NPPV therapy for OSA. The lung-protective ventilation strategies and limiting the positive airway pressures can help reduce the risk of pulmonary barotrauma with CPAP.