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Introduction: Tracheobronchopathia osteochondroplastica (TPO) is a rare benign disorder of the lower part of the trachea and the upper part of the main bronchi.   Case Report: A case of tracheobronchopathia osteochondroplastica (TPO) diagnosed at the time of intubation in an intensive care unit due to difficulty when advancing the endotracheal tube beyond the vocal cords, is reported. A problem was encountered which had not been reported previously in TPO: repeated cuff rupture at the time of surgical tracheostomy occurred possibly because of bony and cartilaginous tissue located in the tracheal wall.   Conclusion:  In addition to difficulty of intubation, TPO may cause tracheostomy tube cuff rupture, which could be explained due to bonny calcification in the tracheal wall.