Tracheal rupture is an uncommon and potentially lifethreatening complication of endotracheal intubation. We present a case of intrathoracic tracheal rupture in a female patient who required emergent endotracheal intubation for acute respiratory distress related to chronic obstructive pulmonary disease exacerbation. Possible contributing factors to tracheal injury included overinflation of the tube cuff, chronic obstructive pulmonary disease, and chronic steroid use. The patient underwent surgical repair without complication. Postoperatively, the tube cuff was placed far distally, close to the carina, and mechanical ventilation was performed using low tidal volume and PEEP in order to avoid high ventilatory pressures.