INTRODUCTION: Diverticulosis seldom causes life threatening hemorrhage and is frequently found in the large bowel. Rare cases of small bowel diverticula are most notably known to appear in the duodenum. Even rarer are severe small bowel diverticulum bleeds in the jejunum with one study noting approximately 50 cases reported in the literature. Due to the difficult location, many have gone unidentified and ultimately resulted in small bowel resections. We present a 58-year-old man with a life threatening jejunal diverticular bleed that was diagnosed and treated conservatively. CASE DESCRIPTION/METHODS: A 58-year-old Hispanic male with past medical history significant for upper GI bleed requiring multiple transfusions, chronic pancreatitis, and SMA thrombosis presented to the ED for recurrent melena. He was previously admitted for suspected GI bleed with no identifiable source on colonoscopy, EGD, and outpatient capsule endoscopy. On this admission, vitals were hemodynamically stable but labs revealed a hemoglobin of 3.3. After appropriate resuscitation, push endoscopy revealed a bleeding proximal jejunal diverticulum which was tattooed, coagulated with epinephrine and clipped. CTA of abdomen showed a stable dissecting aneurysm in between the origin of the inferior pancreaticoduodenal arcade and jejunal branches. He was stabilized and discharged with follow up. DISCUSSION: Small bowel diverticulosis is usually found incidentally in asymptomatic patients. Because jejunal diverticuli are novelty differentials, often forgotten, diagnosis becomes delayed even with the use of standard endoscopy, resulting in significant morbidity and mortality. Several noninvasive studies can be done initially to assess for bleeding. With advances in technology such as small bowel enteroscopy, specifically push enteroscopy, jejunal diverticulum can be diagnosed earlier and treated with clipping as opposed to surgical resection which has been the mainstay treatment for refractory bleeding. This case brings to light a rare manifestation of small bowel diverticuli where future research could be dedicated. There has been another case with similar presentation in which the patient also had history of a SMA clot. This poses the question of whether there is a correlation and if it could be explained by the compromised integrity of the small bowel wall due to the lack of blood flow making it easier for diverticuli to arise there. It also raises the question as to why certain patients are more predisposed to developing these outpouchings.