We present a case of a 33-year-old female that underwent a laparoscopic Roux-En-Y gastric bypass 5 months prior that subsequently developed a gastrojejunostomy stricture treated with endoscopic balloon dilation. Following her third balloon dilation she developed severe abdominal pain and was found to have free air on an upright abdominal x-ray. The patient was immediately brought to the operating room for a diagnostic laparoscopy which demonstrated an anterior perforation of the gastrojejunostomy anastomosis. The decision was made to revise the anastomosis by performing a stricturoplasty where the perforation was extended longitudinally and closed transversely with interrupted silk sutures to both repair the perforation and resolve the anastomotic stricture. The patient had an uncomplicated postoperative course. Gastrojejunostomy strictures are a common complication after laparoscopic Roux-En-Y gastric bypass. There are multiple factors that may lead to the formation of a stricture including marginal ulcers or technical error. Anastomotic strictures are often managed endoscopically with serial balloon dilations. However, if endoscopy fails to relieve the stricture, the patient may need to undergo a laparoscopic gastrojejunostomy revision, which can be morbid. Additionally, anastomotic perforation represents a surgical emergency that warrants immediate exploration. This case presents a unique situation where both situations are present and more conservative measures such as endoscopic stenting are not feasible. By performing a revision stricturoplasty, we attempted to repair the perforation as well as lengthen the anastomosis to relieve the stenotic area.