Multiple tracheal diverticulosis is a rare clinical entity. Tracheal diverticula are usually recognized radiologically as solitary right paratracheal air collections on thoracic computed tomography examination. They are usually asymptomatic but can occasionally present with persistent symptoms. We herein report the case of a 50-year-old male patient who underwent extensive evaluation for persistent cough. Multiple posterior right paratracheal air collections were recognized on thoracic multidetector computed tomography examination, which was confirmed as multiple-acquired posterior upper tracheal diverticula on flexible bronchoscopy. The patient improved with conservative medical management.