Despite improvements in preoperative patient optimization, refinements in surgical methodology and technology, and the implementation of enhanced recovery protocols, complications following gastrointestinal (GI) surgery remain a fact of life. As the rates of GI surgical procedures increase worldwide, so will the volume of complications. The surgical management of complications is often not ideal, as some (such as acute staple line bleeding or the development of an anastomotic stricture) are luminal-based processes that are difficult to approach from an extraluminal (i.e., surgical) perspective. Endoscopy has largely replaced surgery for the management of such postoperative problems. Leak, the most feared complications of GI surgery, can result from intestinal resection, anastomosis formation, or from iatrogenic injury. With advancements in both diagnostic and therapeutic endoscopy, novel endoluminal and transluminal management options for leak continue to evolve. In centers where these interventions are readily available, they are becoming a first-line treatment option. This article will review the endoscopic management of GI complications with a particular focus on the management of postoperative strictures and of full-thickness GI tract defects (perforations, acute leaks, and chronic fistulae).