A physiologically fit 91-year-old gentleman presented with sudden onset chest pain, breathlessness and cardiovascular compromise associated with vomiting. He was treated for renal colic, community-acquired pneumonia and pulmonary embolism before a formal diagnosis of Boerhaave's syndrome was made. The patient was prepared for emergency surgery, unfortunately his condition deteriorated rapidly and he was subsequently managed conservatively. He died 2 days later. Diagnosis and treatment of Boerhaave's syndrome are often delayed. Treatment options for Boerhaave's syndrome include conservative measures, endoscopic interventions and surgery. Chest pain is a common presentation on the acute medical take. Boerhaave's syndrome is a rare cause of chest pain, which may mimic other conditions but should not be missed due a high death rate.