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Jejunal diverticulosis is a rare condition seen in 1-2% of the population and is asymptomatic in 80% of its patients. It can however rarely produce life threatening complications such as perforation, bleeding and obstruction. Diagnosis is often delayed in such patients causing high mortality. We report a 79 year old gentleman presenting with intestinal obstruction for 2 days with peritoneal signs. CT revealed jejunal dilatation with twisting of mesentery with whirlpool sign and closed loop obstruction of jejunum. A differential diagnosis of Jejunal diverticulosis should be considered when encountering patients in the elderly age group in an emergency setting.