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Background: The presence of endometrial tissue in the tracheobronchial tree, pleural, and lung is normally referred to as thoracic endometriosis. The association of catamenial pneumothorax, catamenial haemothorax, catamenial haemoptysis and pulmonary nodules is referred to as thoracic endometriosis syndrome (TES). TES is rare but not as rare as it has always been thought of. Case summaries: Case 1: We present EA, a 26-year-old chef/baker who presented to our unit on account of recurrent cyclical right sided chest pain and difficulty in breathing, recurrent haemoptysis and cyclical abdominal pain and swelling with multiple tender umbilical nodules. On general physical examination she was found to be in respiratory distress but not cyanosed with peripheral arterial oxygen saturation 97% on room air. Examination of the chest revealed a right sided chest fullness and reduced movement with breathing. Percussion note was stony dull and absent of breath sound on right hemithorax. Abdominal examination revealed a moderately distended abdomen with positive fluid thrill. Both Pleurocentesis (thoracocentesis) and paracentesis abdominis yielded a haemorrhagic fluid acellular and pleural and lung biopsy demonstrated endometrial stroma and glands. Imaging examination by way of chest X-ray showed a homogenous opacity of the right hemithorax, and pulmonary nodule following drainage. A diagnosis of Thoracic Endometriosis Syndrome was made. She had VAT with lung and pleural biopsy, pleural abrasion and a thoracostomy tube drainage. Case 2: We present IAE, a 29year-old Po+0 who presented to our unit on account of recurrent cyclical right sided chest pain and difficulty in breathing, unproductive cough. On general physical examination she was found to be in moderate respiratory distress but not cyanosed with peripheral arterial oxygen saturation of 98% on room air. Chest examination revealed an apical flattering of anterior chest wall with left trachea deviation. Percussion note was stony dull on the right lower third and hyper resonance middle and upper zones of right hemithorax. Pleurocentesis (thoracocentesis) yielded air and haemorrhagic fluid acellular and pleural and lung biopsies demonstrated endometrial stroma and glands. Imaging examination by way of chest X-ray and chest CT-scan showed air fluid level of the right hemithorax. A diagnosis of TES was made. She had Laparoscopy and VAT at the same sitting with pleural and lung biopsies. She was managed medically after closed thoracostomy tube drainage. She had partial collapse of right lower lobe and thoracotomy with right lower lobectomy was planned but patient declined. She also had Stage IV endometriosis by (rASRM)/ENZIAN systems Case 3: We present JA a 29-year-old lady, a filling station attendant who presented to our unit with a history of gradual onset of right sided chest pain, progressive difficulty in breathing and non-productive cough, and abdominal pain and swelling. On general physical examination she was found to be in respiratory distress but not cyanosed with SPO2 of 98% on room air. Examination of the chest revealed a right apical flattening, reduced ipsilateral chest movement with breathing. Percussion notes were stony dull and absent air entry on the ipsilateral hemithorax. Abdominal examination showed a mildly distended abdomen with a positive shifting dullness. Both Pleurocentesis (thoracocentesis) and paracentesis abdominis yielded a haemorrhagic fluid acellular at cytology and pleural and lung biopsy demonstrated endometrial stroma and gland. Imaging examination by way of chest X-ray showed a homogenous opacity of the right hemithorax. A diagnosis of Familial Thoracic Endometriosis Syndrome (FTES). Had USS guided lung and pleural biopsy and a thoracostomy tube drainage. She had chemical pleurodesis with tetracycline Conclusion: Thoracic endometriosis syndrome is the diagnosis in a lady of reproductive age who present with cyclic or a cyclical recurrent right sided chest pain, cyclical or a cyclical dyspnoea, haemoptysis, cyclical or a cyclical abdominal swelling and peritonitis.