Introduction. Saber-sheath trachea is a rare malformation of the trachea marked with coronal narrowing with concomitant widening of sagittal diameter, with a sagittal-to-coronal diameter ratio exceeding 2:1. As tracheal rings are stiff and do not collapse around the tube, the intubation is difficult. Case Report. A 53-year-old female was referred to our hospital due to failed intubation at the local hospital during a planned surgery of skin melanoma. The patient was scheduled for surgery in our hospital, her case was presented to a panel of anesthesiologists and she was prepared for surgery. The intubation failed again, even though a video-assisted laryngoscope and endotracheal tube with 5 mm internal diameter was used. The anesthesiologist noticed that the endotracheal tube entered the trachea only 2 cm due to strong resistance, so further intubation was not an option in order to avoid damaging the trachea. The surgery was performed in local anesthesia with analgosedation. Later on, computed tomography was done, because of suspected pathological process compressing trachea, but the radiologist described the anomaly as saber-sheath trachea. One year later, the patient presented with axillary lymph node metastases and needed another surgery. This time the anesthesiologist knew about the trachea malformation, anticipated difficult intubation and used i-gel TM for airway management. Conclusion. Despite the fact that numerous methods have been developed for the purpose of identifying patients at risk of difficult intubation, there are many unexpected airway pathologies that can lead to failed intubation. Adequate preoperative assessment, knowledge of Guidelines for Difficult Intubation Management, availability of supraglottic airway devices, and cooperation between the surgeon and anesthesiologist, are crucial to successful patient management.