Congenital midgut malrotation, a rare anatomic anomaly that can lead to duodenal or small bowel obstruction, rarely is recognized beyond the first year of life. We report a case of unrecognized congenital midgut malrotation that resulted in midgut volvulus, causing intestinal obstruction and requiring emergent reoperation after laparoscopic cholecystectomy. This unusual complication, first reported in 1994, involved a 56-year-old man and resulted in cecal infarction recognized and treated on the second postoperative day. This second case describes a less acute postoperative course, with multiple bouts of partial bowel obstruction leading to two readmissions and finally resulting in a reexploration and definitive treatment on the 19th postoperative day.