Endoscopic placement of a self‐expandable metal stent (SEMS) has become a mainstream treatment to relieve non‐resectable distal malignant biliary obstructions—its longer patency and cost‐effectiveness were demonstrated in comparison with plastic biliary stents in several randomized controlled trials. Despite advances in ERCP devices and SEMSs themselves to enable safe and effective biliary drainage via a SEMS, several significant aspects of the endoscopic placement of SEMS must be considered; otherwise, SEMS‐related complications and early SEMS dysfunction may occur. Also, SEMS dysfunction, including occlusion and migration, occurs at a certain frequency in the long term, and appropriate reintervention is necessary to preserve the quality of life of the patient. Here, we present tips for endoscopic transpapillary SEMS placement for distal malignant biliary obstruction and reintervention for SEMS dysfunction.