Catamenial pneumothorax is a rare condition with accumulation of air in the pleural space with secondary collapse of lung occurring at the time of menses. First documented in 1958 with an incidence of 3-6% of spontaneous pneumothorax and about 1- 1,00,000/year. Usually presents at 3rd or 4th decade and most commonly seen on the right side. There is no single definite etiology for the condition. Catamenial pneumothorax is a rare entity characterized by recurrent accumulation of air in the thoracic space during menstruation usually on the right side. Catamenial pneumothorax is associated with a high rate of recurrence. It has been associated with thoracic endometriosis, yet varying clinical courses and the lack of consistent intraoperative findings have led to conflicting etiologic theories. We report a case of a 18-year-old woman with recurrent bilateral catamenial pneumothorax. She had a history of menstrual-related chest pain and bilateral pneumothorax during hospitalization. When pneumothorax occurs temporally with menstrual cycles, catamenial pneumothorax should be suspected. Video-assisted thoracoscopy is a safer and less invasive modality of therapy.