Colorectal surgery has undergone an enormous technical evolution with the advent of laparoscopy and, more recently, the robotics approach. Technology, combined with the use of more advanced materials and the implementation of pre-habilitation and enhanced recovery after multimodal surgery programs, has allowed the performance of complex surgeries with excellent results. As a result, reaching optimal oncological, physiological, and cosmetic results associated with the patient’s better and shorter postoperative stay is possible. However, colorectal anastomosis is still a critical aspect of this process that always affects the final result of the surgery. Therefore, it has profound implications in the short, medium, and long term. When an anastomotic leak occurs, it is usually the surgeon’s biggest nightmare and can have devastating consequences for both the patient and the surgeon. This chapter’s aim pretended to reflect on how to avoid colorectal anastomotic leakage and, if it happens, how to detect and treat it early, trying to minimize the number and the consequence.