This report presents the case of the emergency repair of a radiation-induced aortoesophageal fistula (AEF) with an endograft. The patient presented with multiple episodes of upper gastrointestinal bleeding. The fistula was discovered and treated in the operating room. The placement of a temporary aortic endograft was successful. The patient unfortunately exsanguinated while awaiting definitive aortic and esophageal repair. The potential occurrence of AEF should be considered in any patient presenting with massive hematemesis without a clear source of the bleeding. Although the patient succumbed to the fistula, this case illustrates the cryptic nature of an AEF and the difficult issues that are inherent in its treatment.