We reviewed a total of 13 stent (Gianturco-Rosch biliary Z-stent) placements in 11 patients with biliary obstruction due to malignancy and report the cases treated with the stent-in-stent technique for treatment of stent occlusion due to tumor ingrowth. Causes of biliary obstruction included cholangiocarcinoma (four cases), hepatic hilar metastasis of gastrointestinal carcinoma (five cases), and pancreatic carcinoma (two cases). After transient percutaneous transhepatic biliary drainage (PTBD), the stents were successfully inserted by transhepatic route in all patients without any serious complication that needed further surgical intervention. Almost all patients were freed from the external PTBD tube about a week after stent placement and discharged from the hospital with improvement in quality of life as well as normal serum bilirubin levels. The technical advantages of stent placement include ease of insertion and the ability to drain both right and left biliary systems from a single transhepatic route by arranging the stents in a variety of configurations. Furthermore, it provides a second chance of stent placement when the previous stent has been occluded by tumor ingrowth.