We report a case of a spontaneous esophageal hematoma in an anticoagulated patient with atrial fibrillation previously complicated by a cerebrovascular accident. A multidisciplinary discussion resulted in holding of anticoagulation until the esophageal hematoma resolved. The patient was managed nonoperatively and discharged, but returned with a new neurologic deficit 3 weeks later. Aspirin treatment was resumed. After complete resolution of hematoma on outpatient scans, warfarin treatment was restarted. The challenges of managing an esophageal hematoma in a patient requiring anticoagulation are discussed.