Anastomotic leakage after oesophagectomy is a dreaded complication. It has a wide range of presentations ranging from the patient being totally asymptomatic to septic with multi-organ failure. From the literature, in general, cervical anastomoses have a higher leakage rate than those that are intra-thoracic, but leaks from the latter confer greater morbidity. Cervical anastomotic leaks that are truly confined to the neck can be managed conservatively, but can extend into the mediastinum and result in more serious complications. Herein, we report on a patient with an oesophago-gastric anastomosis constructed in the neck but with extension into the mediastinum. Subsequently, the patient developed a fistulous erosion into the tracheobronchial tree, which was successfully managed endoscopically.