We present the case of a patient with the rare disorder tracheobronchopathia osteochondroplastica who underwent laparoscopic cholecystectomy. After induction of general anaesthesia, we faced difficulties passing the tracheal tube beyond the vocal cords despite bronchoscopic assistance. With a smaller tube, and by using rotating movements, we managed to successfully intubate the trachea. Because of the irregular tracheal surface, however, ventilation was challenging due to a massive cuff leak. Repeated repositioning did not improve this leak. Only cuff overinflation led to adequate ventilation, though we were cognisant of the increased risk of tracheal wall injury with this approach. After completion of the surgery, the patient's trachea was extubated without complication. This case showed that even with good preparation, intra-operative problems can occur with abnormal subglottic airway anatomy. In some circumstances, these problems can only be solved by compromise. There are no professional consensus or guidelines that can be followed as guiding references for such a case, which can lead to indecisiveness.