Sump syndrome - a collection of digested food, debris, stones, bile, and bacteria in a poorly drained, bile duct reservoir - occurs most commonly after a side-to-side choledochoduodenostomy. As choledochoduodenostomies are now less common, sump syndrome is more often characterized as a complication of Roux-en-Y hepaticojejunostomies; however, most cases occur at the hepaticojejunostomy anastomosis. We report a rare case of sump syndrome in the intra-pancreatic remnant common bile duct in a patient with primary sclerosing cholangitis following living donor liver transplant via Roux-en-Y hepaticojejunostomy. Our patient had a history of end-stage liver disease secondary to primary sclerosing cholangitis but presented with recurrent bacteremia and symptoms of acute cholangitis following her transplant. While this complication has not been reported in this population, we know that those with primary sclerosing cholangitis and those undergoing liver transplantation are at very high risk for biliary complications and strictures. Liver transplant is currently our only treatment for primary sclerosing cholangitis, and more than any other group, they are referred for living donor liver transplantation, preferably via Roux-en-Y hepaticojejunostomy. Thus, our patient's clinical scenario is not uncommon and demonstrates a source of serious infection of which providers must be aware.