A 57-year-old man treated with Coumadin for an episode of paroxysmal atrial fibrillation presented to the Emergency Department with progressive dysphagia and odynophagia. Physical examination revealed a large right-sided lateral and posterior pharyngeal wall mass. Laboratory studies were significant for an international normalized ratio (INR) of 5.4 with a white blood cell count of 11,600/muL and a hematocrit of 33.2%. A lateral soft tissue radiograph and computed tomography (CT) scan of the neck demonstrated a retropharyngeal hematoma compromising the airway. Rapid reversal of the coagulopathy was achieved with fresh frozen plasma and vitamin K. Patients with space-occupying retropharyngeal masses present a significant management dilemma. The choice between observation, intubation, or a surgical airway intervention must rely upon knowledge of the natural course and high rate of airway occlusion when faced with a patient who presents with a retropharyngeal hematoma. Once symptoms of airway compromise manifest, the airway must be expeditiously secured before complete obstruction occurs. This diagnosis should be sought when an anticoagulated patient presents with upper airway symptoms.