Closed-loop gastric outlet obstruction (GOO) is a rare complication that results from a mechanical obstruction in the pylorus or duodenum. In the early 1990s, the common cause of GOO was peptic ulcer disease, accounting for 5% to 10% of hospital admissions. Peptic ulcer disease is the disruption of the mucosal integrity in the stomach and duodenum and can be categorized into gastric ulcers and duodenal ulcers. With the treatment for Helicobacter pylori and the increased use of proton pump inhibitors (PPI), GOO now occurs in fewer than 5% of patients with duodenal ulcer disease and even less in those with gastric ulcer disease. Although the morbidity of duodenal ulcers has been declining in recent years, the incidence of post-bulbar duodenal ulcer (PBDU) remains at a constant 9.33%, primarily due to diagnostic and therapeutic difficulties. Additionally, fewer than 5% of obstructing duodenal ulcers are caused by PBDU, and even fewer are located in the second or third portions of the duodenum. Ulcers located in the distal part of the duodenum raise concern for syndromes associated with hypersecretion of acid, including Zollinger-Ellison syndrome (ZES). The ZES is rare, accounting only for 0.1% of all duodenal ulcers. Here, we present a case where a patient with esophageal stricture developed a rare case of closed-loop GOO secondary to a duodenal ulcer. The patient, initially treated for esophageal perforation, developed an esophageal stricture. The patient was being worked up for ZES and multiple endocrine neoplasia link type 1 (MEN1) syndrome due to his concerning laboratory findings and rare clinical presentation.