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A 78 year old man with a history of chronic lymphocytic leukaemia and prostate cancer presented with repeated vomiting and dyspnoea. Examination showed right sided dullness, and breath sounds were absent. A chest x ray showed right sided consolidation and pleural effusion, and routine blood tests confirmed sepsis. He did not respond to antibiotic treatment. Computerised tomography seven days later confirmed a ruptured oesophagus. Boerhaave's syndrome—spontaneous rupture of the oesophagus to the left side (rarely to the right) following forceful vomiting—should be considered, especially if conventional treatment fails.fails.