Esophageal perforation after anesthesia is rare. It is usually secondary to esophageal instrumentation. Only one case of barogenic rupture after regional anesthesia has been reported. We report two additional cases and present possible mechanisms for this unusual entity. Neither patient had anatomic abnormalities by history or preoperative endoscopy. However, both patients and the previously reported patient had esophageal dysmotility resulting from advanced age, alcoholism, intraoperative medications, and preexisting disease. Each patient experienced at least one episode of emesis with subsequent perforation of the distal one third of the esophagus. The previously reported patient died; both of our patients underwent successful surgical repair and are alive 2 years later. Intraoperative or postoperative emesis in patients with esophageal dysmotility appears to be the principal factor causing esophageal rupture after regional anesthesia. Prevention of nausea and vomiting and recognition of this high-risk population may minimize this complication in the future.