Herniation of the transverse colon and volvulus of it occurring through the previous surgical drain site, presenting as intestinal obstruction, has never been reported. We present an 80-year-old female who complained of abdominal swelling for 10 years. She started developing pain abdomen for 10 days and obstipation for three days. Abdominal examination showed a tender mass in the right lumbar region, with all borders being distinct, and there was no cough impulse. There is a lower midline scar from the previous laparotomy and a small scar over the swelling (drain site). Imaging studies were diagnostic of large bowel obstruction due to the herniation and volvulus of the transverse colon through the previous surgical drain site. She underwent laparotomy, derotation of transverse colon with hernia reduction, and onlay meshplasty. She had an uneventful postoperative course and was discharged.