Bouveret’s syndrome refers to a gastric outlet obstruction secondary to impaction of a gallstone in the pylorus or proximal duodenum. Thus, it can be considered a very proximal form of gallstone ileus and is infrequent. We describe such a unique case that a female patient presents with Bouveret’s syndrome and concomitant common bile duct obstruction by a second gallstone. The decision over its surgical management is complicated, based on risk factors, clinical presentations, radiographic evidence, surgical risk assessment, and specific considerations tailored to individual case. Because of her stable clinical picture and low surgical risk, we proceeded with stone extractions, fistula take-down, and common bile duct exploration in a one-stage procedure. Her postoperative course was complicated by bile stained drainage through closed suction drain that resolved with conservative management.