A diagnosis of primary aortoenteric fistula is difficult to make despite a high level of clinical suspicion. It should be considered in any elderly patient who presents with upper gastrointestinal bleeding in the context of a known abdominal aortic aneurysm. We present the case of young man with no history of abdominal aortic aneurysm who presented with massive upper gastrointestinal bleeding. Initial misdiagnosis led to a delay in treatment and the patient succumbing to the illness. This case is unique in that the fistula formed as a result of complex atherosclerotic disease of the abdominal aorta, and not from an aneurysm.