Jejunal diverticula are rare and the condition remains mostly asymptomatic. However, they can present with vague chronic abdominal symptoms and, in some cases, acute life-threatening complications, such as gastrointestinal (GI) bleeding, bowel obstruction and perforation. We present a case of an adult male who presented with life-threatening GI bleeding secondary to jejunal diverticular disease. Whilst there are undoubtedly more common causes of GI bleeding, this case demonstrates that jejunal diverticular disease should remain on the differential diagnosis and investigations to confirm the diagnosis should be considered. However, despite investigations, the diagnosis may remain elusive and in patients with on-going bleeding, laparotomy and surgical resection is currently the treatment of choice.