An acquired tracheal pouch or diverticulum can be a sequel to congenital esophageal atresia-tracheoesophageal fistula repair. There are variable clinical presentations of this complication, which can be misdiagnosed as asthma. We report a patient with recurrent pneumonia and chronic cough with history of esophageal atresia/tracheoesophageal fistula repair that was dually diagnosed and successfully managed.