Various techniques and interventions have been developed in an effort to obviate gastrointestinal anastomotic leaks. This review is intended to delineate potential modifications that can be made to reduce the risk of anastomotic leaks following gastrointestinal surgery. It may also serve to aid in identifying patients who are at increased risk of anastomotic leak. Modifiable risk factors for leak discussed include malnutrition, smoking, steroid use, bowel preparation, chemotherapy, duration of surgery, use of pressors, intravenous fluid administration, blood transfusion, and surgical anastomotic technique. Based upon literature review, operative techniques should include minimizing operative time, reducing ischemia, and utilizing stapled anastomoses. Buttressing of anastomoses with omentum has proven utility for esophageal surgery. Further recommendations include 5-7 days of immune-modifying nutritional supplementation for malnourished patients, discontinuation of smoking in the perioperative period, limiting steroid use, utilization of oral antibiotic preparation for colorectal surgery, avoidance of early operations (,4 weeks) following chemotherapy, limiting pressor use, and the utilization of goal-directed fluid management.