Diagnosis and management of malignant hilar biliary obstruction is a challenging problem for endoscopists. By using a systematic team approach that incorporates extensive noninvasive imaging and consultation with other specialties including hepatobiliary surgery and oncology, hilar tumors can be successfully approached with endoscopic retrograde cholangiopancreatography (ERCP). However, ERCP, with a conventional approach for diagnosis and drainage, often results in poor outcomes because of incomplete staging and tissue diagnosis, long- and short-term complications of stenting and ineffective palliation. As a result, patients with hilar obstruction are often referred to interventional radiologists, with similarly unsatisfactory outcomes as well as the need for external drainage. The key to optimizing outcomes is careful evaluation for resectability prior to considering ERCP. If surgical resection is not feasible, the primary goal of ERCP should be palliation of jaundice. The best results with ERCP are generally obtained via magnetic resonance cholangiopancreatography and computer tomography-targeted selective unilateral drainage with self-expanding metallic stents. With this approach, safe and effective drainage can usually be achieved, and bilateral stenting and/or percutaneous drainage are rarely necessary.