Despite vast improvements in training of colorectal surgeons and the care of patients undergoing colorectal resections, contemporary series still show an anastomotic leak rate of 1-19%, which continues to contribute to the morbidity and mortality to these patients. New technologies and more recent studies investigating factors affecting the integrity of colorectal anastomosis have been published. Understanding the factors that increase the risk of anastomotic leak allows surgeons to take steps to prevent and ameliorate these risks. We aim to present an evidence-based narrative review relating anastomotic failure and an algorithm for early detection.