This is a 56 year-old male who presented with abdominal pain, nausea, and vomiting. He had undergone a three-stage thoracoscopic-laparoscopic esophagectomy with cervicotomy and gastric pull-up procedure with pyloroplasty 6 months prior for a mid-esophageal cancer. He was doing well until he presented with abdominal pain for one week, with a CT scan performed showing a large amount of herniated bowel into the left chest, with PO contrast stopping at the diaphragm indicative of a small bowel obstruction. He was taken to the OR urgently for laparoscopic reduction of the hiatal hernia and repair. Upon exploration of the abdomen, the majority of the small bowel was found in the left chest in the hernia sac, along with the distal half of the colon and significant omentum. These were reduced easily and the task became approximating the hiatus around the gastric conduit without kinking or strangulation. Adhesions were carefully taken down between the right crus and surrounding peritoneum, liver, and gastric conduit in order to create a posterior space behind the conduit. The crura were approximated posteriorly with sutures taking care not to angluate the conduit, and anteriorly the large defect was covered by an inverted biosynthetic absorbable keyhole mesh, sutured to the crura.