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Intestinal obstruction from gallstones is a rare complication of gallstone disease. These ectopic gallstones can cause obstruction anywhere from the duodenum to the colon and are accompanied by a cholecystoduodenal/enteric/colic fistula. We report an 81-year-old male who presented with gallstone obstruction of the duodenum who underwent attempted endoscopic fragmentation and extraction that eventually led to small bowel obstruction from an impacted fragment of the stone. He underwent successful enterolithotomy and has been asymptomatic from the cholecystoduodenal fistula. Surgery is the gold standard for the treatment of this condition but the extent of the operation remains a matter of debate.