The development of surgical staplers devised for laparoscopy has enabled advancements in complex laparoscopic procedures, such as gastric bypass. This procedure, considered by many as the gold standard for bariatric surgery, is now frequently performed laparoscopically, with the advantages inherent in the minimally invasive approach. Technical failure of surgical staplers is, however, a well known complication of these devices in digestive surgery. We report the case of a leak of the bypassed stomach into the abdominal wall through a trocar site following laparoscopic gastric bypass. The mechanisms responsible for this life-threatening complication and the options to avoid it are discussed.