Duodenal ulcers are a known surgical emergency; however, unknown is the exact incidence, management, and complications of large perforations of duodenal ulcers, especially in regards to previous bariatric surgery. A giant perforated duodenal ulcer presents unique challenges in management. We present a case of a 45 year old gentleman with a remote history of vertical banded gastroplasty and abdominal pain. Workup ultimately revealed a chronic complex large ulcer with erosion of the vertical banded gastroplasty. Endoscopic and medical management was initially attempted but ultimately the patient required surgery. The patient underwent a laparoscopic lysis of adhesions, removal of the vertical banded gastroplasty band, subtotal gastrectomy with roux-en-y reconstruction, duodenal stump closure, and suture ligation of bile duct leaks from the erosive ulcer cavity created by the perforation. The patient did have a takeback to the OR and later presented with a duodenal stump leak; ultimately, the patient did well not only from healing from his ulcer but also improved his BMI. While giant perforated duodenal ulcer is rare, even more so in the context of bariatric surgery, laparoscopic surgical repair in this patient was safe. Expertise in bariatric revisions at a tertiary center is recommended.