Introduction: Painful neck swelling is a common emergency complaint but can present diagnostic challenges. Eagle syndrome is a rare clinical entity in which a pathologically elongated styloid process or ossified stylohyoid ligament produces a constellation of symptoms in the head and neck region. Case Report: We present the case of a 50-year-old male with a spontaneous, atraumatic fracture of an elongated styloid process associated with hematoma formation and radiological findings of airway impingement. Discussion: The classic triad for Eagle syndrome consists of unilateral cervicofacial pain, globus sensation, and dysphagia. Diagnosis of Eagle syndrome should be made based on a combination of physical examination and radiological findings. Treatment options vary based on severity of symptoms. Conclusion: Although more likely to be an indolent and progressive complaint, providers in the acute care setting should be familiar with Eagle syndrome due to the potential for a spontaneous fracture of an elongated styloid process to cause acute, painful neck swelling and life-threatening airway compromise. [Clin Pract Cases Emerg Med. 2020;4(2):197–200.]