Jejunal diverticulosis is a rare gastrointestinal condition manifested as benign outpouching from the jejunal wall. It is usually asymptomatic, but may present as obscure gastrointestinal bleeding. This condition is often found incidentally in the imaging work-up of patients with other gastrointestinal conditions. We present a case of jejunal diverticulosis in a 65-year-old gentleman with obscure overt gastrointestinal bleed.