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Background: Since 1990’s the use of self-expanding metal stent has been known. Initially, this kind of technique has been debated in literature. Actually, is a widely used technique for treatment of bowel neoplastic obstruction. This procedure is important to restore bowel canalization but is feasible performed by expert endoscopists and a dedicated anesthesiologist team. More difficult seems to be the treatment of strictures longer than 9 cm of large bowel or synchronous very close stenosis of rectal-sigmoid junction and rectum. This technical note demonstrated how SEMS positioning can be performed for treatment of long and extreme large bowel obstruction. Methods: In this case series we have treated all patients admitted in our department with diagnosis of extreme bowel neoplastic obstruction, with “stent in stent” technique, in deep sedation. Results: From January to August 2019 we admitted in our Surgical and Endoscopic Unit two patients, a 90- year-old for bowel obstruction by synchronous colorectal cancer and a 80-year-old female for 15 cm large bowel neoplastic obstruction. Patients were submitted to “Stent-in-Stent” technique. No complications and perforation were observed with restore of bowel canalization after few hours from SEMS positioning. Both patients had no signs of bowel obstruction at abdomen X-Ray control, after 48 hours. 80-year-old female patient was submitted to left colectomy after 6 days without complications, while 90-year-old was discharge after 3 days. Conclusion: This study demonstrated how is possible to perform endoscopic SEMS positioning to treat longer than 15 cm neoplastic large bowel obstruction and synchronous colorectal cancer with “Stent-inStent” technique. Our technical note describes, point by point, all passages of this procedure and suggests as is possible to treat synchronous sigmoid-rectal neoplastic obstruction using two different kind of metal stent.