Arterial-enteric fistulas occur from a multitude of causes, especially following surgical manipulation of vasculature. The development of an iliac artery-enteric fistula (IEF) occurs rarely in patients with failed pancreatic transplants. IEFs warrant urgent intervention due to the high mortality from hemorrhagic and septic shock. The diagnosis can be delayed by a lack of suspicion, the low sensitivity of diagnostic tests, and the nonspecific signs of fistulas on computed tomography. The management of IEFs is adapted from guidelines for arterial-enteric fistulas of other causes, with little consensus on ideal vascular reconstruction and postoperative antimicrobial management. The outcomes are limited to the short-term results from case reports and case series. We report two cases of IEFs in patients with a history of simultaneous pancreatic kidney transplant. Our patients underwent successful resolution of gastrointestinal bleeding and sepsis, with definitive management of fistula resection and interposition iliac artery bypass. The index of suspicion for IEFs should be high, and they should be considered as a source of anemia or gastrointestinal bleeding of an unknown source in patients with failed pancreatic transplant. Definitive management should be pursued in patients who can tolerate fistula resection, allograft explant, and arterial reconstruction.