Tracheal stenosis refers to a reduction in the size of the tracheal lumen and can be due to a myriad of reasons, but the most common remains trauma. In iatrogenic situations, internal trauma is the most likely culprit, resulting from prolonged intubation. Our case reviews a patient who developed severe tracheal stenosis (90% reduction in lumen size) within a month of a threeday- long intubation, and presented to the emergency room with dyspnea, orthopnea, and stridor. Tracheal reconstruction with resection of the stenosed segment and end-to-end anastomosis was done. The patient returned a month later with re-stenosis, and underwent tracheal dilatation. Subsequently, he was discharged with a tracheostomy with no problems thereafter.