This case presents a 46-year-old woman with bowel obstruction due to two separate diaphragmatic hernias—one containing small bowel and the other containing colon—following a complex surgical history including Roux-en-Y gastric bypass and prior hernia repairs. Exploratory laparotomy revealed extensive adhesions and previous mesh placement. The small bowel was easily reduced, while the colon required careful dissection. Both hernias were repaired using pledgeted sutures anchoring the diaphragm to the abdominal and chest walls. The case highlights challenges in managing recurrent diaphragmatic hernias in patients with altered anatomy.