Acquired tracheomegaly is a rare condition associated with pulmonary fibrosis, connective tissue disease and the use of cuffed tracheal tubes. We describe the urgent tracheal re-intubation and subsequent tracheal repair of a previously well 58-year-old man who developed tracheostomy-related tracheomegaly during prolonged mechanical ventilation for coronavirus disease 2019 pneumonitis. Urgent tracheal re-intubation was required due to a persistent cuff leak, pneumomediastinum and malposition of the tracheostomy tube. We describe the additional challenges and risks associated with airway management in patients with tracheomegaly, and discuss how even in urgent cases these can be mitigated through planning and teamwork. We present a stepwise approach to tracheal re-intubation past a large tracheal dilatation, including the use of an Aintree catheter inserted via the existing tracheal stoma for oxygenation or tracheal re-intubation if required. Computed tomography imaging was valuable in characterising the defect and developing a safe airway management strategy before starting the procedure. This report emphasises the role of planning, teamwork and the development of an appropriate airway strategy in the safe management of complex cases.