Sump syndrome is a rare complication of biliary-enteric anastomosis. Classically, the distal bile duct becomes obstructed by gastrointestinal debris after choledochoduodenostomy, resulting in cholangitis or, less commonly pancreatitis. Obstruction of the biliary tree by gastrointestinal contents after Roux-en-Y choledochojejunostomy or hepaticojejunostomy has not been described in the English-language literature. This report details the diagnostic and operative management of the first patient with sump syndrome after hepaticojejunostomy. The presumed pathophysiology was reflux of vegetable matter up the efferent limb, resulting in hepatic duct obstruction and cholangitis. The patient ultimately required complex choledochoscopic drainage of the intrahepatic biliary tree and revision of the previous Roux-en-Y hepaticojejunostomy.