This is a report of an unusual patient who had four of the five manifestations of thoracic endometriosis, including right pneumothorax, left hemothorax, chest pain, and hemoptysis. This patient shows that recurrence of symptoms can occur while a patient is receiving hormonal replacement therapy even after hysterectomy and bilateral salpingo-oophorectomy; estrogen replacement should probably be delayed for several months to allow complete regression of the ectopic endometrial tissue. Alternatively, chemical pleurodesis can be effective in treating recurrent pneumothorax or hemothorax while the patient is receiving hormonal replacement. Bilateral pleural involvement and hemoptysis suggest microembolization of endometrial tissue as the pathogenic mechanism for thoracic endometriosis.