Self-expanding metal stent (SEMS) placement offers safe and effective palliation in patients with upper gastrointestinal obstruction due to a malignancy. Well described complications of SEMS placement include tumor growth, obstruction, and stent migration. SEMS occlusions are treated by SEMS redeployment, argon plasma coagulation application, balloon dilation, and surgical bypass. At our center, we usually place the second SEMS into the first SEMS if there is complete occlusion by the tumor. We discovered an unusual complication during SEMS redeployment. The guidewire passed through the mesh of the first SEMS and caused the second SEMS to become entangled with the first SEMS. This led to the distortion and malfunction of the second SEMS, which worsened the gastric outlet obstruction. For lowering the risk of entanglement, we studied stone extraction balloon-guided repeat SEMS placement. This is the first report of a SEMS entangled by the mesh of the first SEMS and stone extraction balloon-guided repeat SEMS placement for lowering the risk of this complication.