<p>Tracheal reconstruction surgeries pose significant anaesthetic challenges requiring individualised airway management strategies.&#xa0;This retrospective case series describes four adult patients (aged 28–62 years) undergoing tracheal reconstruction for post-procedural stenosis (<i>n</i> = 2), tracheal mass (<i>n</i> = 1), and idiopathic stenosis (<i>n</i> = 1). Preoperative evaluation included bronchoscopy, CT imaging, and pulmonary function tests. Airway management strategies, ventilation techniques, and perioperative outcomes were analysed.&#xa0;Various techniques were employed including awake fibreoptic intubation, cross-field ventilation, cardiopulmonary bypass, and tracheostomy. Main challenges included maintaining oxygenation during critical surgical phases and postoperative extubation decisions. Two patients were extubated in the operating room; two required postoperative ventilation. No mortality occurred; all patients had favourable outcomes at follow-up.&#xa0;Successful anaesthetic management of tracheal reconstruction surgeries requires meticulous preoperative evaluation, individualized airway management strategies, and close communication with surgical teams. Fibreoptic intubation is the gold standard but may fail, necessitating backup plans including cardiopulmonary bypass for complex cases.</p>