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Purpose To propose the imaging classification of true tracheal bronchus (TTB) on multi-detector computed tomography (MDCT), and to evaluate its anatomical relationship with surrounding structures. Materials and Methods This study included 44 patients who were diagnosed with TTB on MDCT for 6 years. We classified TTB into five types, based on the existence of the right upper lobe bronchus originating from the right main bronchus and the number of segmental bronchi of TTB. We analyzed the site of origin and the running direction of TTB based on its anatomical relationship with surrounding structures and some ancillary findings. Results The imaging classification of TTB included Type I (47.7%), Type II (13.6%), Type III (11.4%), Type IV (25.0%), and Type V (2.0%). According to the site of origin of TTB, below the aortic arch (52.3%) and at the level of the aortic arch (43.1%) were the two main sites of origin, whereas the frequency of the site of origin above the azygos arch, at the level of the azygos arch, and below the azygos arch was 27.3%, 38.6%, and 34.1%, respectively. Considering both aortic and azygos arches, below the aortic arch and below the azygos arch were the most common sites of origin (27.3%). With respect to the running direction of TTB, in all cases, TTB passed below the azygos arch to the right upper lobe. There was no statistically significant (p > 0.05) difference in age or sex between types of TTB. Ancillary findings included tracheal stenosis (n = 2), narrowing of the right main bronchus (n = 2), luminal narrowing of TTB and bronchiectasis at the distal portion (n = 1), and a highly located azygos arch above the aortic arch (n = 2). Conclusion The proposed imaging classification of TTB and its anatomical relationship with surrounding structures will improve our understanding of various imaging features and embryological development of TTB. Radiologists should pay careful attention to evaluation of the airway including the trachea on thoracic imaging.