Gastrointestinal obstruction is a common preterminal event in patients with gastric and pancreatic cancer who often undergo palliative bypass surgery. Although endoscopic palliation with self-expandable metallic stents has emerged as a safe and effective alternative to surgery, experience with this technique remains limited. In particular, a proximal jejunal obstruction requires more technical expertise than a duodenal obstruction. Palliative treatment modalities include both surgical and nonsurgical approaches. In this report, we describe the successful placement of self-expandable metallic stents at the proximal jejunum using a combination of percutaneous endoscopic, intraoperative, and transstomal stenting. Usually endoscopy is not indicated in cases of proximal jejunal obstruction, but some cases may require palliative endoscopy instead of bypass operation.