This case of Boerhaave's Syndrome had several unusual features including a delayed presentation and right-sided esophageal perforation. The patient's initial episode of hematemesis may have been caused by a small mucosal laceration in the area of the Barrett's lesion that later ruptured. On the other hand, if initially there was an esophageal rupture, it did not violate the parietal pleura or mediastinum. The overlying pleura remained intact until digested by gastric contents, thereby causing a right-sided hydropneumo thorax and a marked increase in symptoms, which promoted the patient to come to the ED. Because the patient initially appeared stable and had a history of emesis 4 days before presentation, and because an initial chest X-ray interpretation overlooked the right-sided apical pneumothorax, Boerhaave's Syndrome was not considered initially. Aspiration pneumonia, pancreatitis, alcoholic gastritis, or active peptide ulcer disease were in our initial differential. It was only after the repeat chest X-ray, which more obviously showed the pneumothorax, and insertion of the chest tube that the correct diagnosis was made. Had the pneumothorax not been overlooked initially, the diagnosis may have been made earlier. It is apparent from this case and a review of the literature that Boerhaave's Syndrome is an uncommon clinical entity and has varying modes of presentation, making the diagnosis a difficult clinical challenge. Boerhaave's Syndrome should be considered in all ill-appearing patients presenting with the combination of gastrointestinal and respiratory complaints. The single most important test may be the upright chest X-ray. However, if it is normal, and there is a high index of suspicion, esophagograms and or chest CT may be required to demonstrate the lesion. Because survival is directly related to the time to diagnosis and treatment, a high clinical suspicion can decrease the substantial morbidity and mortality associated with Boerhaave's Syndrome.