Tracheal stenosis is a rare and life-threatening condition. If left undiagnosed, this can lead to failed intubation, surgery postponement, or additional invasive airway management. A high index of suspicion from attending anesthesiologists due to inconsistencies between patient’s symptoms and diagnostics could lead to a more accurate diagnosis and management. This is a case of a 24-year-old female with difficulty breathing who was initially assessed as a case of glottic mass. The dilemma between the patient’s presentation and the preidentified airway obstruction led the anesthesiologist to do further investigation. A quick upper airway evaluation was done using the flexible fiber-optic scope which unexpectedly showed a 70%–80% circumferential subglottic stenosis. Management was henceforth changed to tracheal resection and reconstruction to address this new finding. Meticulous planning, preparation, and transdisciplinary approach of communication with the surgical team alongside detailed knowledge are probably the most important factors in the management of tracheal stenosis.