Airway stents are commonly used to palliate malignant central airway obstruction and tracheo-/bronchoesophageal fistulas. Despite their efficacy in immediately relieving airway obstruction, they can be associated with a variety of complications. We report the case of a 44-year-old woman with a malignant bronchoesophageal fistula treated initially with a self-expanding silicone mesh stent in the left main bronchus followed 2 weeks later by an esophageal stent. Shortly afterward, she presented with chest pain, worsening cough, and breathlessness. A CT scan of the chest revealed the airway stent in the contralateral mediastinum perforating the right main bronchus. We discuss her subsequent management and complications associated with self-expanding airway stents in this setting.