Abstract Boerhaave’s syndrome is the spontaneous transmural rupture of the esophagus. Patients can have a variety of manifestations. Boerhaave’s syndrome has to be considered in acutely ill patients with no other explanations for their illness. Computed tomography scan of the chest is emerging as a useful tool for the evaluation of these patients. Surgical repair is the standard of care. Adequate drainage of the pleural fluid is necessary to prevent pulmonary complications. Esophageal perforation should be considered whenever thoracostomy tube drainage assumes an enteric character. When inserting the chest tube for draining pleural fluid, the trochar should not be used because of potential injury to the already perforated esophagus. Posterior placement of the chest tube should be avoided because the tube may migrate into the perforated esophagus. Because of the high incidence of mortality, prompt suspicion, diagnosis, and management are warranted. A careful history, detailed review of the imaging, and a high index of suspicion are key for prompt diagnosis.