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Obstruction of the duodenum by an abdominal aortic aneurysm (AAA) (aortoduodenal syndrome) has rarely been reported. It presents with symptoms of upper gastrointestinal (GI) tract obstruction. Obstructive jaundice caused by an AAA is also extremely rare and requires high clinical suspicion. We present a unique case with informed consent of an elderly gentleman who presented with both rare presentations over a course of few months. After extensive literature search, we have found case reports of patients showing either of the two unusual presentations, but none were found to show them together.