Oesophagectomies and gastrectomies are performed predominantly for the treatment of malignant disease. However, in this case series, we describe three patients with benign disease who had a laparoscopic oesophagogastrectomy with gastroduodenal detachment and Roux-en-Y biliary diversion, and discuss the operative feasibility and consequent patient outcomes. Our aim was to modify the procedure using an established reconstruction already practised in gastric and bariatric surgery, thereby preventing operative sequelae that lead to a poor quality of life (eg reflux oesophagitis and vomiting). During the first postoperative year, our first two patients experienced weight loss, indigestion and lower bowel symptoms with no apparent improvement in gastric function compared with a standard gastric tube pull-up reconstruction. In the longer term, in both patients, the gastric tube interpositions appeared to function well and there was no evidence of gastro-oesophageal reflux disease, delayed gastric emptying or troublesome indigestion. Our third patient, who had lifelong severe reflux symptoms, was eating normally three months after the operation with no need for antacid medication. We therefore conclude that laparoscopic Ivor–Lewis oesophagogastrectomy with Roux-en-Y bypass is a more complex reconstruction with added risks but may in the long term result in better overall outcomes and satisfaction for patients, particularly those with benign disease.