Tracheal wall disruption is a rare complication of endotracheal intubation, typically occurring in the posterior (membranous) trachea lacking cartilaginous support. We present the case of a 68-year-old man who developed an anterior tracheal tear after routine endotracheal intubation, most likely occurring secondary to protrusion of a factory-preloaded stylet beyond the distal orifice of the endotracheal tube. Tracheal disruption should be considered in any patient with subcutaneous emphysema and respiratory distress after tracheal extubation and confirmed with bronchoscopy. Conservative management may be appropriate for those with small tears, hemodynamic stability, and the ability to isolate the tear from positive pressure ventilation.