Esophageal obstruction represents an endoscopic emergency owing to the high mortality rate associated with complications, including perforation and airway compromise. While typically caused by food or foreign body ingestion, esophageal clot represents a rare etiology of obstruction. We present a case of esophageal obstruction in the context of an anastomotic stricture and chronic anticoagulation for atrial fibrillation caused by clot formation due to oral hemorrhage after dental extractions. Clot retrieval was accomplished via endoscopic suction, and balloon dilation of the anastomotic stricture was performed to prevent recurrence. Our case illustrates the importance of considering oral hemorrhage, therapeutic anticoagulation, and esophageal strictures as risk factors for esophageal obstruction due to clot formation in order to make a timely diagnosis and treatment of this potential endoscopic emergency.