A 54-year-old man with squamous cell carcinoma of the tongue underwent bilateral cervical lymph node dissection, total tongue resection, forearm flap reconstruction, and tracheostomy. The plan was to replace the oral endotracheal tube (ETT) with a cuffed tracheostomy tube at the end of the surgical case while the patient was still under general anesthesia. No major complications were expected as the tracheal foramen was visible once surgical access was obtained. However, removal of the ETT and subsequent placement of the tracheostomy tube failed twice. Successful ventilation was not observed via capnography, and the patient’s peripheral oxygen saturation (SpO₂) dropped to 70%. The anesthesiologist concluded that securing the airway through the tracheostomy would be difficult. The patient was immediately reintubated orally at which time his SpO₂ was 38%, and he was successfully resuscitated and recovered without any sequelae. This rare situation was one we had not encountered previously, so we retrospectively analyzed all tracheostomy cases performed by our department from the past 3 years. Data from 54 patients who underwent tracheostomy tube exchange after tracheostomy were aggregated from their medical records and compared with our patient. Excluding the conditions during surgery, we surmised that tracheal depth, S/H ratio, and body weight were identified as potentially significant risk factors for failed tracheal tube placement or exchange.