A 74 year old woman was consented for laparoscopic Roux en Y gastric bypass reversal due to a history of refractory gastrojejunostomy marginal ulcers with a severe anastomotic stricture. She had undergone prior laparoscopic Roux en Y gastric bypass followed by emergency repair of an anastomotic ulcer perforation, and later on, an elective laparoscopic gastrojejunostomy revision. The gastrojejunostomy stricture and anastomotic ulcers recurred and required subsequent endoscopic balloon dilations with medical therapy with Sucralfate and proton pump inhibitors. The laparoscopic gastric bypass reversal was performed without intraoperative complications, with a negative gastrogastrostomy endoscopic leak test. The Roux limb was resected to prevent blind-loop syndrome and bacterial overgrowth, but it was divided just proximal to the jejunojejunostomy without anastomotic takedown while transecting it too close to the anastomosis. This caused a delayed ischemic small bowel perforation 16 days later at the jejunojejunostomy transection staple line. An emergency exploratory laparotomy was performed with repair of the perforation in addition to peritoneal lavage and drain placement. She recovered and went home 2 weeks later on IV antibiotics and antifungal. The patient has recovered well and is off antibiotics and antifungal, tolerating a regular diet.