Sclerosing cholangitis is a chronic cholestatic liver disease defined by both inflammatory and fibrotic changes of the biliary tract leading to diffuse stricture formation. This entity exists in both a primary and secondary form. Here we present a rare case of secondary sclerosing cholangitis due to direct metastasis from a gallbladder adenocarcinoma. A 55-year-old morbidly obese male presented electively with a 2-week history of low back pain and scleral icterus for 2 days. He also described severe epigastric pain that worsened postprandially and a 13 kg weight loss over the previous month. The patient denied any personal or familial history of malignancy or prior liver disease. Laboratory evaluation revealed mild elevation of transaminases with moderately elevated alkaline phosphatase and total bilirubin. Imaging included ultrasound and contrast-enhanced computed tomography of the abdomen and pelvis showing multiple large gallstones and a large tissue density mass within the fundus of the gallbladder. Subsequent endoscopic ultrasound was performed revealing celiac and portal lymphadenopathy with fine needle aspirations demonstrating adenocarcinoma. Over the next 15 days, bilirubin progressively increased. Magnetic resonance cholangiopancreatography was unremarkable. Liver biopsy, performed to exclude other etiologies of liver failure, demonstrated biliary cholestasis. Endoscopic retrograde cholangiopancreatography was then performed and an occlusion cholangiogram revealed diffuse multifocal stricturing of the intrahepatic bile ducts and moderate stenosis of the common bile duct without proximal ductal dilatation. Thus secondary sclerosing cholangitis due to gallbladder adenocarcinoma was diagnosed.