Colorectal cancer (CRC) is one of the most common malignancies in the world. Despite significant improvements in surgical technique, postoperative complications still occur in a fair percentage of patients undergoing colorectal surgery. The most feared complication is anastomotic leakage. It negatively affects short-term prognosis, with increased post-operative morbidity and mortality, higher hospitalization time and costs. Moreover, it may require further surgery with the creation of a permanent or temporary stoma. While there is no doubt about the negative impact of anastomotic dehiscence on the short-term prognosis of patients operated on for CRC, still under discussion is its impact on the long-term prognosis. Some authors have described an association between leakage and reduced overall survival, disease-free survival, and increased recurrence, while other Authors have found no real impact of dehiscence on long term prognosis. The purpose of this paper is to review all the literature about the impact of anastomotic dehiscence on long-term prognosis after CRC surgery. The main risk factors of leakage and early detection markers are also summarized.