The aim of this article is to present strategies for preventing and managing the failure of the surgical restoration of intestinal continuity. Despite improvements in surgical technique and perioperative care, anastomotic leaks still occur, and with them occur increased morbidity, mortality, length of stay, and costs. Due to the devastating consequences for patients with failed anastomoses, there have been a myriad of materials and techniques used by surgeons to create better intestinal anastomoses. We will also discuss the management strategies for anastomotic leak when they do inevitably occur.