Background: Esophageal stents are a widely used treatment method for various esophageal pathologies such as malign and benign obstruction and contained perforations of the esophagus. The aim of this study was to identify the risk factors affecting esophageal stent failure rates. Methods: A total of 469 patients receiving esophageal stents were included in this retrospective observational study. The stents were inserted between January 2005 and December 2013 in a single tertiary center. Primary outcome was stent failure, classified as any major complication related to the stent or the need to replace or urgently remove the esophageal stent. Results: Esophageal cancer was found in 331 (70.6%) patients, whereas non-esophageal cancer in 79 (16.8%) and benign esophageal disease in 59 (12.6%) patients. Dysphagia was the most common symptom indicating the stent insertion with 371 (79.1%) patients, perforation being the second most common (N=33, 7.0%). Stent failure rate was 34.3% (N=161), with median time to stent failure of 75 days (24–161 days). Multivariate Cox proportional hazards analysis showed stent location in the middle third of the esophagus to carry a higher risk for stent failure compared to distal esophagus [hazard ratio (HR) =1.818, 95% confidence interval (CI): 1.26–2.63, P=0.002]. Stent length of 12–15 cm was associated with higher risk of stent failure than stent lengths of Conclusions: Stent failure is more prevalent when stenting the mid-esophagus, using longer stents or after performing esophageal dilatation prior to stenting.