Spontaneous pneumothorax associated with menstruation is a rare entity named catamenial pneumothorax. A 36-year-old woman presented with recurrent right-sided pneumothorax requiring repeated chest tube insertions. She underwent video-assisted thoracoscopy (VATS). Histopathology was suggestive of thoracic endometriosis. When spontaneous pneumothorax occurs in ovulating women in relation to menstruation catamenial pneumothorax should be suspected. Correct diagnosis will lead to effective treatment and prevention of recurrences