Tracheal diverticulum is a rare chronic airway pathology with cystic protrusions from the trachea or main bronchi and has insufficient epidemiological documentation. The article describes the case of a patient with thyroid cancer and known airway stenosis, who was not diagnosed with a tracheal diverticulum before surgery. Perioperatively, the endotracheal tube was repeatedly repositioned into an undiagnosed diverticulum, causing critical intubation failure and complicated tracheostomy. Under fiberoptic bronchoscopic guidance, the tracheal tube was successfully advanced through the right subglottic diverticular opening into the left tracheal lumen, achieving secure placement in the true tracheal cavity. A retrospective analysis of published cases characterizes the pathological features of tracheal diverticulum. In patients with elective surgery and a suspected tracheal diverticulum, especially after a previous cervical procedure or pathology, preoperative bronchoscopy is recommended to confirm the defect and adjust airway management. Transnasal fiberoptic bronchoscope-guided intubation effectively rescues an unexpected difficult airway during reintubation associated with tracheal diverticulum.