A biliary fistula which may occur spontaneously or after surgery, is an abnormal communication from the biliary system to an organ, cavity or free surface. Spontaneous biliary-enteric fistula is a rare complication of gallbladder pathology, with over 90% of them secondary to cholelithiasis. Approximately 6% are due to perforating peptic ulcers. Symptoms of biliary-enteric fistula varies widely and usually non-specific, mimicking any chronic biliary disease. Cholecystoduodenal fistula causing severe upper gastrointestinal (UGI) bleed is very rare. Bleeding cholecystoduodenal fistula commonly requires surgical resection of the fistula and repair of the duodenal perforation. We describe the case of a previously healthy older patient who initially presented with symptoms suggestive of UGI bleeding. Bleeding could not be controlled endoscopically. When a laparotomy was performed, a cholecystoduodenal fistula was discovered and bleeding was noted to originate from the superficial branch of cystic artery.