This case report describes a 57-year-old man who developed an aorto-esophageal fistula after receiving two covered metallic stents for esophageal adenocarcinoma. He presented with a massive hemorrhagic shock from hematemesis. Imaging revealed a fistula between the descending thoracic aorta and the upper end of the lower esophageal stent. Emergency placement of an aortic endoprosthesis sealed the fistula and stopped the bleeding. Late hemorrhagic complications like aorto-esophageal fistula can occur in a small percentage of patients who receive esophageal stents, especially after prior radiation therapy, and may require urgent endovascular management to control bleeding.