Despite the overwhelming limitations that plague the literature surrounding the optimal method of reestablishing pancreatico-enteric continuity following a Whipple operation, it is clear that all successful techniques conform to sound surgical principles. These principles include a water-tight and tension-free anastomosis, preservation of adequate blood supply for both organs involved in the anastomosis, and minimal trauma to the pancreas gland. Although surgeon experience, gland texture, and pancreatic duct size are clearly the dominate risk factors from a long list of variables associated with pancreatic leaks following pancreatoduodenectomy, these are nonmodifiable covariates. Although the plethora of current literature cannot provide a single definitive technical solution for restoring pancreatico-enteric continuity, a small number of well-designed RCTs support the use of transanastomotic external stenting for high-risk pancreatic glands and an end-to-side invaginated pancreaticojejunostomy. The truth remains that an individual surgeon's mastery of a specific anastomotic technique, in conjunction with a large personal experience, is likely to be the best predictor of a low pancreas leak rate following pancreatoduodenectomy.