Two cases of combined tracheal and oesophageal stenting for carcinoma of the upper oesophagus invading the tracheo-bronchial tree are described. Case 1 describes the complication of respiratory distress following insertion of a high oesophageal stent. This caused severe stridor which required tracheal stenting. In case 2 prophylactic stenting of the airway prior to oesophageal stenting was performed as a staging CT demonstrated severe compromise of the distal trachea/bronchus in a patient who was experiencing both dysphagia and dyspnoea. In both cases the respiratory and dyspnoeic symptoms were relieved. These cases illustrate the effective use of tracheal/bronchial and oesophageal metal stents in palliating patients with combined respiratory and dysphagic symptoms secondary to oesophageal malignancy. When treating high oesophageal tumours tracheal compromise should be considered and prophylactic stenting of the airway prior to oesophageal stenting performed to avoid further airway compromise when the oesophageal stent expands.