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This article describes the case of a male patient in his late 40s with a history of pulmonary tuberculosis (TB) 25 years ago who presented with a decade-long recurrent cough, sputum production and frequent pneumonia. His symptoms were repeatedly wrongly credited to TB reactivation or reinfection, leading to several unnecessary courses of anti-tubercular therapy. A decisive high-resolution CT thorax revealed the pathognomonic features of Mounier-Kuhn syndrome such as marked tracheobronchomegaly and airway diverticulosis. This provided an appropriate explanation for his clinical course. This case highlights a critical diagnostic pitfall, emphasising the need to consider structural airway diseases in patients with a history of TB whose symptoms follow an atypical or refractory pattern, thereby avoiding unnecessary treatments and guiding appropriate management.