Despite the dramatic decrease in cuff-related complications with the introduction of high-volume low-pressure devices for intubation and tracheostomy, notable problems can still occur. A case is reported of a patient who developed persistent dilatation of the trachea after prolonged mechanical ventilation. This is an under-recognized, life threatening clinical entity occurring after cuffed intubation for prolonged time. At present there is no definitive treatment regarding the management of a dilated trachea on a ventilator-dependent patient and therefore emphasis is directed at prevention. The patient presented was managed with periodical alterations of the cuff level which although not achieving any reversal of the dilatation, have prevented further progression of tracheal damage. During the follow-up period, regular assessment with flexible endoscopy has provided more reliable information on the condition of the trachea than computed tomography (CT) scanning.