Management of intrathoracic anastomotic leakage after esophagectomy by means of endoscopic stent insertion has gained wide acceptance as an alternative to surgical reintervention. Between January 2004 and March 2013 all patients who underwent esophagectomy at a German high-volume center for esophageal surgery were included in this retrospective study. The study comprises 356 patients. Anastomotic leakage occurred in 49 cases. There were no significant differences in age, American Society of Anesthesiologists (ASA) score, or frequency of neoadjuvant therapy between cases with and without leak. However, leak patients sustained significantly more often postoperative pneumonia, pleural empyema, sepsis, and acute renal failure. Moreover, leak victims had higher odds for fatal outcome (16 of 49 vs 33 of 307; odds ratio, 5.94; 95% confidence interval, 2.65 to 13.15; P < 0.0001). The leakage was amendable by endoscopic stenting in 29 cases, whereas rethoracotomy was mandatory in 20 patients. Between stent and rethoracotomy cases, we observed no significant differences in age, ASA score, neoadjuvant therapy, occurrence of pneumonia, pleural empyema, or tracheostomy rate. Rethoracotomy patients sustained more often sepsis (16 of 20 vs 14 of 29; P = 0.04) and acute renal failure (nine of 20 vs four of 29; P = 0.02) as expression of more severe septic disease. Nevertheless, there was no significant difference in mortality (seven of 29 vs nine of 20; P = 0.21). Furthermore, we observed three cases of stent-related aortic erosion with peracute death from exsanguination. Despite being the preferred treatment option, endoscopic stenting was only feasible in approximately 60 per cent of all intrathoracic leaks. The results are marred by the occurrence of deadly vascular erosion. Therefore, individualized strategies should be preferred to a general recommendation for endoscopic stenting.