An aortoesophageal fistula (AEF) is an exceedingly rare and life-threatening cause of upper gastrointestinal bleeding, particularly in patients with vascular prostheses. Endoscopic findings in such cases are scarcely described. We describe a 73-year-old male admitted to the emergency department with hematemesis and altered consciousness. His history included ascending thoracic aortic dissection repair with endovascular prosthesis placement 25 years prior. Upon admission, he presented with signs of hypovolemic shock and hemoglobin of 6.5 g/dL. Following hemodynamic stabilization, upper gastrointestinal endoscopy revealed a mid-esophageal rupture, characterized by a pulsatile, violaceous, firm protrusion, without active bleeding.