Intestinal anastomosis is an essential part of surgical practice, and with it comes the inherent risk of complications including leaks, strictures, and bleeding, which result in significant morbidity and occasional mortality. Understanding the myriad of risk factors and the strength of the data helps guide a surgeon as to the safety of undertaking an operation in which a primary anastomosis is to be considered. This article reviews the risk factors, management, and outcomes associated with anastomotic complications.