Abstract Background Oesophageal reconstruction post-oesophagectomy is performed for both benign and malignant pathologies. Generally, the stomach is the conduit of choice due to its simplicity, requiring only one anastomosis. However, in some cases the stomach may not be a viable option immediately or at all, and alternatives must be considered. We describe a case where the stomach was not immediately viable and two cases where alternative conduits were sought. Furthermore, we discuss techniques such as ‘supercharging’ and ‘superdrainage’ which enhance arterial flow and venous drainage respectively, in order to prevent ischaemia and related complications of the anastomosis site. Methods and Results Case 1 presents a 72-year-old with an incarcerated para-oesophageal hernia leading to necrosis of the distal oesophagus and proximal stomach. After resection, a feeding jejunostomy and a loop oesophagostomy in the neck was created. Months later, the oesophagostomy was closed, and the residual stomach was carefully mobilised into the thorax while preserving the gastro-epiploic arcade, and oesophago-gastric anastomosis was performed. Case 2 involves a 68-year-old female who had elective Nissen fundoplication for a hiatus hernia, which recurred early with strangulation of the distal oesophagus and proximal stomach requiring emergency oesophago-gastrectomy. She later underwent a colonic interposition using the left colon, with superdrainage through an anastomosis between a branch of the middle colic vein to the left external jugular vein. Case 3 describes a 61-year-old male with a gastro-oesophageal adenocarcinoma treated with an Ivor-Lewis oesophagectomy. A year later, he suffered from a strangulated diaphragmatic hernia causing necrosis of the gastric conduit. This was replaced with an isoperistaltic colonic interposition using the transverse and left colon with super drainage. Unfortunately, three years later, this was again complicated with pancreatitis and perforated gall bladder with associated ischaemia of the colonic conduit. A re-do of the colonic interposition using the right colon was done with an arterial graft between the right transverse cervical artery and branch of ileal artery and super drainage via a branch of the ileal and right external jugular veins. Conclusion Primary and in particular secondary re-constructions of the UGI tract are complex procedures and individual approaches are needed as residual anatomy varies. Consequently, such cases require meticulous planning and a multidisciplinary approach involving the cardio-thoracic, plastic and vascular surgeons and adequate support by the anaesthetic and intensive care team. Although associated with significant morbidity and mortality, reestablishment of a swallowing passage is often desired by patients to maintain quality of life.