Catamenial pneumothorax is defined as recurrent and spontaneous pneumothorax occurring within 48 to 72 hours of the onset of menstruation. The etiology is unknown but several theories have been proposed. This is the case of a 45- year- old G2P2 with an eight- year history of on and off chest pain and difficulty of breathing coinciding with menstruation that resolved spontaneously. On two occasions of intractable pulmonary distress during menstruation, diagnosed as spontaneous pneumothorax, thoracostomy, thoracotomy, and mechanical, and eventually, chemical pleurodesis were performed. With a clinical diagnosis of catamenial pneumothorax, continuous oral contraceptive pills were given while patient was being stabilized. When OCP's were discontinued 9 months after, the pulmonary symptoms promptly recurred. Total abdominal hysterectomy with bilateral salpingooophorectomy (THBSO) was finally performed. Patient has remained asymptomatic more than 2 years after surgery. The management of catamenial pneumothorax may be initiated based on clinical signs and symptoms in the face of possible catastrophic complications which in this case is spontaneous pneumothorax.