Chronic obstructive pulmonary disease (COPD) is one of the leading causes of disability and death worldwide. COPD exacerbation is usually treated with antibiotics, systemic corticosteroids, and inhaled bronchodilators. We present a case of recurrent COPD exacerbation that was treated repeatedly with standard therapy. Dynamic expiratory computed tomography of the chest was done, which revealed concomitant tracheomalacia. COPD and tracheomalacia may coexist during recurrent exacerbations of COPD, and delayed diagnosis can be associated with severe comorbidities. Ordering the appropriate imaging may aid in the correct diagnosis and facilitate appropriate management.