We report a case of small bowel obstruction due to gallstone ileus found in a patient with previous pancreaticoduodenectomy (Whipple procedure). Investigation by computed tomography of the abdomen showed a transition point in the midjejunum due to a radioopaque intraluminal mass. Following resuscitation, the patient underwent laparotomy to remove the offending mass from the midjejunum. Subsequent stone analysis confirmed a cholesterol-rich gallstone. This is thus the first description of gallstone ileus following Whipple procedure. The rarity of this presentation and a literature review is presented.