Endoscopic stent placement is an effective palliative treatment for malignant dysphagia and fistula, leading to rapid symptom relief. However, recurrent dysphagia and other stent-related complications are common, for which reason continuously new design modifications are implemented. Although some of these changes facilitate stent placement, complications remain and occur at similar rates. Recently, stents have also been used in benign esophageal disorders. Covered stents have the ability to effectively seal esophageal perforations and leaks, reducing the need for invasive surgery. This benefit does not pertain to patients with refractory benign esophageal strictures, in whom stents have limited long-term effect and are associated with a high complication rate. The initial results of fully covered metal stents in refractory esophageal variceal bleeding are encouraging, but their definite role remains to be further elucidated. This review provides an overview of indications, techniques, and management of complications of stents in malignant and benign esophageal disease.