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Upper gastrointestinal tract bleedings may represent the first clinical evidence of peptic ulcer and the related surgical emergency is still characterized by a high mortality rate. The presence of multiple complications, rare but possible in case of duodenal ulcer, such as the fistulization in the common bile duct alone or associated to others, can significantly increase the difficulty in the treatment. The Authors report a particularly complex case of a 77 years old male diabetic patient, with chronic bronchopaty, urgently admitted to our department for hematemesis. Soon after his hemodynamic stabilization, the patient was submitted to surgery which showed a duodenal ulcer with penetration/fistulization in the common bile duct associated to a perforation of the gallbladder with intra-hepatic abscess and erosion of the gastro-duodenal artery. Despite unfavourable outcome the case gave us the starting point for a review of the literature primarily related to the rarer biliary complications of duodenal ulcer. Bleeding ulcers today are usually treated by an interdisciplinary approach comprehensive of endoscopy, interventional radiology and, only rarely, surgery. The choice among the available options depends on the clinical presentation of the patient. Despite diagnostic and therapeutic progresses, peptic ulcer may still rarely have a dramatic presentation and be associated to uncommon and difficult anatomical aspects whose diagnosis and treatment may be not easy at all. The knowledge of all the aspects of peptic ulcer pathophysiology is therefore essential for the treatment of these patients.