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A 34-year-old man presented with acute severe left-sided abdominal and flank pain with associated postprandial nausea and vomiting. CT imaging revealed findings suspicious for a closed loop small bowel obstruction. Intraoperative findings were that of a left paraduodenal hernia (of Landzert) secondary to a mesenteric defect immediately posterior to the ascending branch of the left colic artery. The defect was closed via minilaparotomy. Unfortunately, his postoperative course was complicated by small bowel obstruction which required further laparotomy and adhesiolysis. The patient eventually made a good recovery. Here, we present a rare case of intestinal obstruction and discuss the aetiologies and management of this unusual phenomenon.