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Roux-en-Y hepaticojejunostomies (RYHJs) can be associated with biliary complications. We describe a very rare case of gallstone ileus causing a Roux limb obstruction in a patient who had recurrent hepatolithiasis and cholangitis secondary to residual stones despite repeated cholangioscopy. The obstruction was managed with enterotomy and removal of gallstone via an open surgical approach, with complete clearance of hepatolithiasis through on-table trans-enteric cholangioscopy.