A 60-year-old male presented with jaundice. He had a history of extended left hepatectomy, cholecystectomy, hepaticojejunostomy for moderately to poorly differentiated hepatocellular carcinoma, and transverse colectomy for transverse colon cancer. Computed tomography showed hepatocellular carcinoma recurrence in the liver, extending from the hepaticojejunostomy site to the elevated jejunum, resulting in obstructive jaundice. Internal biliary drainage using a percutaneous transhepatic approach was planned. However, the guidewire could not pass through the obstruction caused by the tumor at the hepaticojejunostomy site. After performing hepatic arterial infusion chemotherapy, to reduce the tumor volume, transcatheter arterial chemoembolization was performed for hepatocellular carcinoma recurrence. After transcatheter arterial chemoembolization, the catheter was successfully advanced beyond the tumor at the elevated jejunum owing to tumor shrinkage, thus completing internal biliary drainage.