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Surgical management of oesophageal and gastro-oesophageal junction malignancies is one of the most challenging situations confronting the surgeon. Attaining a complete circumferential resection margin of lower-third oesophageal and gastro-oesophageal junction locally advanced carcinomas requires en-bloc resection of the hiatus and all the peri-oesophageal tissue and pleura. This results in an increased risk of herniation of the abdominal organs through the enlarged hiatus, which carries significant risk of morbidity and mortality.The incidence of this complication is higher than has been reported. Surgical management of symptomatic hernias is the standard treatment while criteria for managing asymptomatic hernias are less clear. We report a rare case of a late mediastinal herniation of the pancreas and bile duct, leading to obstructive jaundice following oesophagectomy which was treated successfully in our unit.