A 39-year-old woman with no known risk factors presented for a recurrent upper gastrointestinal (GI) bleed. She had a prior history of failed kidney and pancreatic transplants secondary to childhood diabetes mellitus type I. After an extensive workup, she was found to have active hemorrhage into an area of the small bowel from an artery supplying her failed pancreatic transplant. Here, we discuss the importance of a systematic approach to evaluation, a high index of suspicion, and a known but not entirely common method of treatment for this condition.