This chapter discusses recalcitrant benign oesophageal strictures, commonly caused by gastro-oesophageal reflux disease or radical radiotherapy for squamous cell cancer of the oesophagus. While most strictures respond to acid suppression and dilatation, long strictures resistant to non-surgical measures may necessitate resection or reconstruction. The case presented involves a 52-year-old female with strictures from chemoradiotherapy, requiring frequent dilatations and experiencing complications like perforation. Due to fibrotic changes and previous interventions, oesophageal bypass was chosen over resection. Using a gastric conduit placed retrosternally, successful reconstruction was achieved, emphasising the importance of careful patient selection and surgical planning in managing such challenging cases.