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Introduction: Bouveret’s syndrome is a rare entity, accounting for 1–3% of gallstone ileus cases. It is more common in elderly females and is associated with significant morbidity and mortality. It presents with epigastric pain, nausea, and vomiting in patients with concurrent cholelithiasis. Given the nonspecific symptoms, the diagnosis is supported with imaging highlighting Rigler’s triad. The therapeutic approach can be either endoscopic or surgical. Case Series: The authors present two cases of Bouveret’s syndrome, managed with two different approaches. The first case is an 82-year-old man presenting with diffuse abdominal pain and distension, nausea, and vomiting. Blood tests showed increased inflammatory parameters and an abdominal computed tomography (CT) scan compatible with Bouveret’s syndrome. Upper gastrointestinal (GI) endoscopy revealed a fistula at D2 level, and an obstruction at D3, caused by a 3 cm gallstone. The patient underwent laser and mechanical lithotripsy for gallstone removal. The second case is a 71-year-old woman presenting with vomiting associated with dehydration and abdominal pain for several days. Blood tests showed increased inflammatory parameters and CT scan showed a bilioduodenal fistula at D2 level, with a 5 cm a gallstone at that level, confirmed in the endoscopy. An attempt to remove the gallstone was performed, without success, so the patient underwent laparotomy with extraction of the gallstone via an anterior gastrotomy. Conclusion: Bouveret’s syndrome is a rare disease that requires thoughtful and tailored management. Given this rarity, there is minimal data to support specific therapy recommendations. Therefore, management should be tailored to the patient at the discretion of the multidisciplinary team and the resources of the institution.