Bouveret’s syndrome is a rare complication of cholelithiasis. It is characterized by a gallstone entering the intestine through a cholecystoenteric fistula, impacting the duodenum and causing gastric outlet obstruction. Rarely, it presents with hematemesis and melena. The diagnosis involves computed tomography (CT) and the treatment depends on the patient’s stability, the location of the obstruction, stone size, and the fistula. Endoscopy or minimally invasive lithotripsy can be considered initially. If this fails, surgical intervention is recommended. We present a case of upper gastrointestinal bleeding (UGIB) preceding the development of Bouveret’s syndrome.