Anterior duodenal ulceration with erosion into the cystic artery is an extremely rare source of upper gastrointestinal hemorrhage. Interventions that have previously been reported include open exploration with cholecystectomy, open exploration while leaving the gallbladder in situ, and angiographic management. We report a case of massive upper gastrointestinal bleeding related to duodenal ulcer penetration of the cystic artery and discuss potential management strategies.