Bouveret syndrome is ectopic gallstone impaction and obstruction of the duodenum or pylorus affecting a small minority of gallstone ileus cases. There have been advances in its endoscopic management, but this remains a challenging condition to treat successfully. We present a patient with Bouveret syndrome who required open surgical extraction and gastrojejunostomy after attempts of endoscopic retrieval and electrohydraulic lithotripsy (EHL). A 79-year-old man with a medical history of gastroesophageal reflux disease, chronic obstructive pulmonary disease on 5 liters of oxygen at baseline, and coronary artery disease with recent stenting presented to the hospital with three days of abdominal pain and vomiting. CT of the abdomen/pelvis demonstrated gastric outlet obstruction, a 4.5 cm gallstone in the proximal duodenum, cholecystoduodenal fistula, gallbladder wall thickening, and pneumobilia. Esophagogastroduodenoscopy (EGD) demonstrated a black pigmented stone impacted in the duodenal bulb with ulceration of the inferior wall. Repeated Roth net retrieval attempts of the stone were unsuccessful even after biopsy forceps were used to trim the stone’s margins. The next day, EGD with EHL used 20 shocks of 200 watts, allowing for partial stone removal and fragmentation, but the majority of the stone remained stuck to the wall. Laparoscopic cholecystectomy was attempted but was converted to an open extraction of the gallstone from the duodenum, pyloric exclusion, and gastrojejunostomy. The gallbladder remained in place, and the cholecystoduodenal fistula was not surgically repaired. The patient experienced significant postoperative pulmonary insufficiency and remained on the ventilator with failure of multiple spontaneous breathing trials. Postoperative imaging showed resolution of pneumobilia but a small amount of contrast leaked from the duodenum revealing the fistula's persistence. After 14 days of unsuccessful ventilator weaning, the family opted for palliative extubation. Advanced endoscopic techniques have been regarded as the first-line intervention for Bouveret syndrome as there is low morbidity and mortality associated with them. However, there is a reduced success rate compared to surgical intervention. Open surgical management has high morbidity and mortality in the elderly and comorbid patients commonly affected by this condition. Thus, the risks and benefits must be weighed and individualized for each patient with Bouveret syndrome before therapeutic intervention.