Subglottic stenosis poses a rare but life-threatening risk for difficult tracheal intubation. Here, we report a unique case of undiagnosed subglottic stenosis discovered during emergency intubation of an 80-year-old woman with type 2 respiratory failure from infective exacerbation of asthma. A small calibre size 5.0 tracheal tube was successfully inserted, but significant difficulties with mechanical ventilation, nebulizations, and secretion management necessitated front-of-neck access with a surgical tracheostomy. Drawing on our experience of this case, we consider the diagnostic and management challenges of subglottic stenosis and discuss the issues of mechanical ventilation through small calibre tubes in patients with severe bronchospasm.