Chronic anastomotic leaks present a daunting challenge to colorectal surgeons. Unfortunately, anastomotic leaks are common, and a significant number of leaks are diagnosed in a delayed fashion. The clinical presentation of these chronic leaks can be silent or have low grade, indolent symptoms. Operative options can be quite formidable and highly complex. Leaks are typically diagnosed by radiographic and endoscopic imaging during the preoperative assessment prior to defunctioning stoma reversal. The operative strategy depends on the location of the anastomosis and the specific features of the anastomotic dehiscence. Low colorectal anastomosis (i.e. following low anterior resection) may require a transanal approach, transabdominal approach, or a combination of the two. While restoration of bowel continuity is encouraged, it is not infrequent for a permanent ostomy to be required to maximize patient quality of life.