Intraluminal duodenal diverticulum (IDD) is a rare congenital anomaly resulting from the failure of the duodenum to recanalize during embryogenesis leaving a duodenal diaphragm or web within the lumen of the duodenum. In theory, the peristaltic force gradually stretches the tissue over time forming a diverticulum within the duodenal lumen. Identification of IDD by endoscopy or diagnostic imaging can be difficult, these lesions can be mistaken for other lesions or the collapsed diverticulum can be overlooked. The median age of presentation is the fourth decade. Although most cases are asymptomatic, some can present with vague abdominal complaints such as bloating, nausea, abdominal discomfort, or pain. Complications of IDD are intestinal bleeding, biliary pancreatic symptoms, intestinal obstruction, and perforation. Management of IDD complications could be challenging since data are limited. We present an unusual case of a 78-year-old female presenting with acute chest pain, palpitations, and incidental findings of IDD and pancreatic divisum. Her course was complicated by recurrent gastrointestinal bleeding and small bowel obstruction.