The Montgomery T-tube is a device used as a combined tracheal stent and an airway after laryngotracheal surgery. The device is used mostly in specialist centres for head and neck surgery, and therefore, many anaesthetists may be unfamiliar with its use. The Montgomery T-tube presents the anaesthetist with challenges both during its surgical insertion when acute loss of the airway might occur and also during induction of anaesthesia in patients who have such a tube in situ. Anaesthetists who are unfamiliar with the tube may have to resort to ingenious ways of coping with the problems of a shared airway with a T-tube, which does not have a suitable adaptor for a standard catheter mount, as well as controlling and maintaining ventilation through the device. Safe management of such patients requires careful planning. We describe the anaesthetic management of two cases to illustrate the problems associated with Montgomery tubes.