We report a case of fatal aorto-oesophageal fistula (AEF) bleeding secondary to a thoracic aneurysm in a 69 year-old woman presenting with hematemesis and back pain. The clinical presentation was unusual, complicated by the coincidence of a bleeding perforated gastric ulcer, which probably led to the late diagnosis of the AEF. Symptoms of AEF are non-specific but with a typical pattern (Chiari's triad). AEF should be suspected in any patient with upper gastrointestinal haemorrhage, midthoracic pain, dysphagia, and typical findings at oesophagoscopy.