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Small bowel obstruction is the most common surgical emergency after a patient has had abdominal surgery. However, Boerhaave syndrome secondary to an ileostomy obstruction has not been reported in current literature. We present a rare case of two concurrent surgical emergencies in a patient with Boerhaave syndrome and small bowel obstruction.A 38-year-old woman presented with sudden onset severe central chest pain associated with breathlessness. She had a history of Crohn's disease, which had been treated with pancolectomy and ileostomy. Clinical examination showed an extensive palpable surgical emphysema extending from the neck to the pelvis with a distended abdomen. Computed tomography contrast of the chest and abdomen reported bilateral pneumothoraces, ruptured oesophagus and distended small bowel secondary to obstruction at the ileostomy. She was referred to the nearest cardiothoracic centre for an urgent assessment. Unfortunately she passed away shortly after the scan.Ruptured oesophagus is associated with a high mobidity and mortality if it is not recognised, so early diagnosis and prompt treatment is crucial in reducing the mortality rate. There is a strong association between stoma formation and incidence of small bowel obstruction but no difference between an ileostomy and colostomy. This case helps to illustrate the challenging management of chronic recurring abdominal obstruction and the delicate balance of risk of complication versus benefit of various management being surgical or conservative. All general surgeons should be wary of the potential complication of oesophageal perforation secondary to intestinal obstruction.