Self-expandable esophageal stents are being commonly used for palliative treatment in advanced esophageal cancer patients to relieve dysphagia, prevent tracheoesophageal fistula, and facilitate symptomatic betterment. The modern covered stents reduce the ingrowth of the tumor but have seen an increase in the incidence of stent migrations. We report a rather complicated presentation of an esophageal stent for esophageal dilatation and a challenging management of a difficult tracheostomy.