Catamenial pneumothorax is defined as 2 episodes of pneumothorax temporally related to the onset of menses, usually within 72 hours. The most common symptoms associated with catamenial pneumothorax are shortness of breath, cough, and pleurisy, with 40% having only chest pain. Catamenial pneumothorax is generally considered the most frequent presentation of thoracic endometriosis syndrome, although histological findings of endometriosis during surgery are rare. Catamenial pneumothorax aetiology is most likely to be multifactor in origin involving a combination of different mechanisms. A multidisciplinary approach of combined VATS and traditional laparoscopy optimally addresses pelvic, diaphragmatic, and thoracic endometriosis in a single operation. Hormonal treatment with GnRH agonist for six months seems to be effective in enhancing surgical results.