Gallstone ileus is a rare complication of cholelithiasis, characterized by mechanical bowel obstruction due to a biliary calculus originating from a bilioenteric fistula. The Rigler triad, consisting of aerobilia, ectopic gallstone, and intestinal obstruction, is rarely observed in its complete form. We present the case of a 92-year-old male with a history of acute lithiasic cholecystitis who presented to the Emergency department with acute epigastric pain. Initial evaluation revealed gallbladder dilatation, gallstones, and gallbladder wall thickening suggestive of acute cholecystitis. During hospitalization, the patient experienced an episode of hematemesis, leading to the diagnosis of a cholecystoduodenal fistula and a large blood clot in the duodenal bulb. Further imaging showed an ectopic gallstone causing small bowel obstruction. The patient underwent urgent surgery for stone extraction, followed by endoscopic intervention for the bleeding vessel identified at a subsequent gastroscopy. Unfortunately, the patient had a poor postoperative course and passed away seven days later. This case report highlights the exceptional occurrence of both the Rigler triad and upper gastrointestinal bleeding in a patient with gallstone ileus. Surgical intervention is crucial for the initial resolution of intestinal obstruction, followed by cholecystectomy and repair of the bilioenteric fistula. Awareness of these rare presentations is important for timely diagnosis and appropriate management of this uncommon complication of cholelithiasis.