Aorto-intestinal fistula is a rare cause of massive upper gastrointestinal bleeding. The authors report on an 82-year-old man who had an aorto-esophageal fistula due to a benign Barrett's ulcer. The patient presented with a sentinel hemorrhage followed by fatal exsanguination despite vigorous attempts at resuscitation. Management of the entity requires awareness, appropriate radiologic and endoscopic investigation and early surgery. Even with appropriate management, the mortality remains high.