Introduction: Intramural esophageal hematoma is a rare condition presenting with dysphagia, nausea and mid epigastric or retrosternal chest pain. We present a unique case of spontaneous esophageal hematoma in a patient anticoagulated with apixaban for atrial fibrillation. Case presentation: An 88-year-old woman with history of hypertension, hypothyroidism, persistent atrial fibrillation on apixaban presented to emergency department with sudden onset epigastric pain, dysphagia and nausea without vomiting while having dinner. Physical examination was unremarkable except for mild tenderness in the epigastric region. Initial workup including complete blood count, complete metabolic panel, lipase, troponin was unremarkable. EKG showed atrial fibrillation with no ischemic changes. CT chest showed abnormal hyperdense mass-like thickening approximately 4 x 3 x 12 cm involving the mid/distal thoracic esophagus with possible differentials being food bolus, esophageal hematoma or mass. Prothrombin complex concentrate (Kcentra) was given as patient was on apixaban and gastroenterology was consulted for upper endoscopy which showed a large hematoma occupying most of the esophageal lumen at the entire length of esophagus. After family discussion on stroke-versus-bleeding risk with anticoagulation, cardiology recommended holding anticoagulation for at least a month and future evaluation for WATCHMAN device. With stable hemoglobin and gradual advancement to a soft diet, patient was discharged home with repeat endoscopy planned in two weeks. Conclusion: Spontaneous esophageal hematoma, although rare in incidence, should be identified as a differential diagnosis in a patient on anticoagulation presenting with chest pain. Literature shows a higher incidence of this complication in women. Timely diagnosis and management along with discontinuing anticoagulation can significantly lower morbidity and mortality and overall has favorable prognosis.