Spontaneous rupture of the esophagus (Boerhaave syndrome) is an extremely rare, life-threatening condition. Traditionally surgery was the treatment of choice. Endoscopic stent insertion offers a promising alternative. The aim of this study was to compare the results of primary surgical therapy with endoscopic stenting. A British and a German high-volume center for esophageal surgery participated in this retrospective study. At the British center, operative therapy (primary repair or surgical drainage) was routinely carried out. Endoscopic stent insertion was the primary treatment option at the German center. Only patients with nonmalignant, spontaneous rupture of the esophagus (Boerhaave syndrome) were included. Demographic characteristics, comorbidity, clinical course, and outcome were analyzed. The study comprises 38 patients with a median age of 60 years. Time between rupture and treatment was less than 24 hours in 22 patients. Overall mortality was four of 38. Diagnosis greater than 24 hours was associated with higher risk for fatal outcome (odds ratio [OR], 4.64; 95% confidence interval [CI], 0.33 to 265.79). The surgery (S) and the endoscopic stent group (E) included 20 and 13 cases, respectively. Esophagectomy was unavoidable in three cases and two were managed conservatively. There were no significant differences in age, time to diagnosis less than 24 hours, intensive care unit days, hospital stay, sepsis, renal failure, slow respiratory weaning, or presence of comorbidity between the two groups. In 11 of 13 in the stent group, operative intervention (video-assisted thoracic surgery, thoracotomy, mediastinotomy) was eventually mandatory and three of 13 even required repeated surgery. The rate of reoperation in the surgery group was six of 20. Mortality was two of 13 (E) versus one of 20 (S). The odds for fatal outcome were 3.3 times higher in the stent group than in the surgery group (OR, 3.32; 95% CI, 0.15 to 213.98). Management of Boerhaave syndrome by means of endoscopic stent insertion offers no advantage regarding morbidity, intensive care unit or hospital stay, and is associated with frequent treatment failure eventually requiring surgical intervention. Furthermore, endoscopic stenting shows a higher risk for fatal outcome than primary surgical therapy.