Intestinal malrotation is a rare congenital condition caused by the absence of or incomplete rotation of the small bowel during the embryonic period and is defined as any deviation from the normal 270 degree counter clockwise rotation of the midgut. If this condition is not timely recognized, it may result in disastrous consequences, such as gangrene of the small gut. 64–80% of cases present primarily during the neonatal period prior to the first month of life, as acute intestinal obstruction due to volvulus of small intestine. The presentation of intestinal malrotation in adults is rare, and occurs in approximately 0.2–0.5%. We present the case of a 17–year–old male who presented to the emergency room with recurrent episodes of colicky abdominal pain and bilious vomiting. Contrast–enhanced computerized tomography (CT) revealed malrotation of the gut with midgut volvulous. Contrast enhanced CT showed the abnormal anatomic location of a right sided small bowel, a left–sided colon and an abnormal relationship of the superior mesenteric vein (SMV) situated to the left of the superior mesenteric artery (SMA) instead of to the right and the characteristic ‘whirpool or whirl sign’ describing the swirling appearance of bowel and mesentery twisted around the superior mesenteric arterial axis with the presence of midgut volvulus. In patients with acute obstruction, this differential should be kept in mind, especially if the patient has no previous abdominal surgery or evidence of tuberculosis.