Complete digestive disunion due to anastomotic necrosis is considered a contraindication to endoscopic repair. However, recent publications have suggested that endoscopic treatment by insertion of a self-expandable metal stent (SEMS) is possible. The report of this patient series aims to demonstrate the use of endoscopic management in selected cases with complete digestive disunion. Seven consecutive patients with complete and circumferential upper gastrointestinal anastomotic disunion were treated at two European tertiary care centers between 2009 and 2021 by endoscopic insertion of an SEMS. Treatment was performed with a therapeutic gastroscope under general anesthesia, carbon dioxide insufflation, and fluoroscopic guidance, after surgical or percutaneous drainage. All patients were successfully treated by endoscopic insertion of fully or partially covered SEMS left in place for a median of 8 weeks, with a median of 3 endoscopic sessions. Digestive neo-epithelialization was associated with a restored circumferential gut lumen in all cases. The rate of stent migration was 23% and three patients (43%) experienced symptomatic strictures, which were successfully treated by endoscopic dilation. Complete digestive rupture could be successfully treated by endoscopy in selected cases, adding proof-of-concept data regarding guided tissue regeneration alongside SEMS placement.