After esophagectomy, there is potential for abdominal contents to herniate through the hiatus alongside the gastric pull up or other conduit used for reconstruction. The presented case describes the evolution of a giant paraconduit hernia and its acute presentation with signs of incarceration. In the operating room, about half the length of the small bowel appeared acutely herniated and was easily reduced. The transverse colon and greater omentum was chronically herniated and required lysis of adhesions for reduction. The hiatal hiatal defect was closed and reinforced with biologic mesh. The patient recovered very well postoperatively with no recurrence on CT two months later.