Introduction <p>Herniation of abdominal contents into the chest after an Ivor Lewis esophagectomy is an infrequent complication of a trans-thoracic esophagectomy.</p> Case Presentation <p>A 37-year-old female underwent an Ivor Lewis Esophagectomy in 2021 for lower esophageal adenocarcinoma and has been on regular surveillance since. She presented 44 months later with abdominal pain, tightness in the chest, vomiting, and mild dyspnoea. A non-contrast computed tomographic scan of the thorax showed a widening of the esophageal hiatus with herniation of the stomach tube and transverse colon into the left chest. The patient underwent an uneventful laparoscopic procedure with a reduction of the hernial contents – stomach and colon, and primary repair of the large diaphragmatic defect. Mesh repair was not required as the defect was safely approximated in a tension-free manner.</p> Conclusions <p>Trans-thoracic diaphragmatic herniation of the colon and the gastric tube into the left chest is an infrequently reported complication of an Ivor Lewis esophagectomy. The hernia can be safely and effectively repaired laparoscopically, preventing future major secondary complications.</p>