Upper gastrointestinal bleeding (UGIB) is a common condition causing a considerable number of admissions in clinics. The most frequent causes of UGIB are peptic ulcer disease, malignancies, variceal bleeding and Mallory Weiss tears. A 47-year-old male subject was admitted to the emergency service with recurrent episodes of melena. He had been hospitalized several times before, but he was discharged because the endoscopic procedures did not reveal any origin. There has been a history of Whipple surgery for pancreatic adenocarcinoma. When admitted he was tachycardic, melanic stool was noted on rectal examination and his hemoglobin level was decreased. Widespread angioectasia was detected at the borders of the biliary-enteric anastomosis, which was known to have bleeding on upper GI endoscopy. Despite their rare presentation, bleeding from the vascular ectasia near the anostomotic line should be kept in mind in the differential diagnosis of patients with gastrointestinal hemorrhage.