Introduction Spontaneous Tonsillar Hemorrhage, also described as Hemorrhagic Tonsillitis , is a rare complication of acute or chronic tonsillitis with a reported incidence of less than 1.1% of all infectious tonsillitis cases worldwide Case Report A 19-year-old male with a history of chronic tonsillitis presented to the emergency department for a three-day history of progressively worsening odynophagia and blood-tinged saliva for greater than 48 hours, and found to have “kissing tonsils” on exam with bilateral exudates and venous oozing. Conclusion Emergent airway assessment is critical in patients presenting with potential airway obstruction. In patients presenting with spontaneous tonsillar hemorrhage, hemostasis should also be achieved, whether topically, or through emergent tonsillectomy should the patient’s clinical status warrant it.