Tracheomalacia (TM) is an under-recognized condition that presents with nonspecific symptoms such as dyspnea, cough, and recurrent infections. Frequently, patients with this condition are misdiagnosed with more prevalent diseases such as asthma and chronic obstructive pulmonary disease. We report a case of a 29-year-old woman with long-standing, mild, persistent asthma characterized by dyspnea and cough, who experienced acute and severe worsening of her symptoms after the cesarean section for the delivery of her third child. She was initially treated with bronchodilators and oral corticosteroids without improvement. She underwent further evaluation with a chest computed tomographic scan and a flexible bronchoscopy, which revealed focal TM in the distal trachea secondary to chronic extrinsic compression due to a pulmonary vascular sling. We discuss her subsequent evaluation and management.