Cholecystoenteric fistulas occur as a result of a chronic inflammatory insult involving the gallbladder and the erosion of both its wall and a bowel segment. When the fistula develops, it creates a pathway for gallstones to migrate and cause an intestinal obstruction, known as gallstone ileus. When it obstructs the gastric outlet, a proximal variant of gallstone ileus occurs, known as Bouveret's syndrome.A 65-year-old man presented to the emergency department with a three-day history of epigastric and right upper quadrant pain and persistent vomiting, preceded by unintentional weight loss of 15 kg over three months. Endoscopic and complementary imaging studies identified a concurrent gastric outlet obstruction caused by a lodged gallstone in the duodenal bulb and gallstone ileus.The patient underwent an urgent exploratory laparotomy and was submitted to an enterolithotomy and gastrolithotomy. Due to a sudden deterioration on the fourth postoperative day, he underwent an emergent re-laparotomy that found fecal peritonitis and complete dehiscence of both closures. The patient was then managed with damage control surgery. An atypical gastric resection and enterectomy of the distal ileum were performed and the patient was admitted to the intensive care unit in temporary abdominal closure (laparostomy). The patient failed to improve and died on the same day. Ultimately, the patient's multiple comorbidities, including morbid obesity, malnutrition, and diabetes, contributed to poor tissue healing and the fatal outcome.Gallstone ileus and Bouveret's syndrome are two rare complications of cholecystoduodenal fistulas that have not yet been reported to occur simultaneously. Both intestinal and gastric obstruction makes the surgical approach the first-line treatment.