Catamenial pneumothorax is a rare complication secondary to pleural endometriosis. We present a case of a 37-year-old-female with a history of recurrent pneumothoraces with an associated temporal relationship to the onset of her menses. In addition to her recurrent pneumothoraces, on further evaluation, she was found to have multiple nodular masses within the omentum. A thoracoscopic biopsy was subsequently performed, which showed endometrial implants within the pleural space and within the omental cavity. The radiological features and pathogenesis of this rare disease are reviewed and discussed with reference to relevant literature.