Interventional internal drainage of the biliary tract has become an established procedure for both the temporary and definitive treatment of biliary obstruction due to malignant or benign disease. Biliary stent migration and stent fracture are known but rare complications. A 50-year-old man presented with acute onset pain in the abdomen and vomiting. He had undergone hepaticojejunostomy following a bile duct injury during open cholecystectomy 13 years before he presented at our institution. Subsequently, he developed a benign biliary stricture at the anastomotic site, which was stented transhepatically by a metallic stent. CT of his abdomen showed a fractured stent segment obstructing the jejunum with a localized perforation. Herein, we discuss his presentation and course of management, and review the factors influencing stent migration and fracture and the potential options for stent retrieval. The patient needed surgical intervention to retrieve the migrated fragment of metal stent and to resect the perforated jejunal segment. The role of endoscopic self-expanding metal stents for benign biliary disease remains controversial. A migrated stent that has become symptomatic should be removed endoscopically in early and accessible cases and surgically when endoscopic measures fail or when complicated by obstruction or perforation.