Connections between the airway and the surrounding structures, whether gastrointestinal tract or pleural space, usually result from cancer or related treatment. The ensuing morbidity depends on the size and location of the fistula. Bronchopleural and tracheoesophageal fistula are some of the more frequent ones. They are managed by either a gastroenterologist or a pulmonologist or as a joint effort. The anesthesia providers should be aware of poor pulmonary reserve, oxygen dependency, ventilation challenges, and potential/ongoing airway obstruction. The specific challenges encountered depend on the type of communication. Those connecting bronchus and pleural space pose different challenges than the connections between bronchus and pleural space. Bronchopleural fistulae typically follow pneumonectomy or lobectomy and are usually diagnosed between 10 and 15 days after surgery. They might respond to conservative measures such as drainage of the infected pleural space, prophylactic antibiotics, and clearance of bronchial secretions. Some of the bronchoscopist’s approaches are sclerosant injections, fibrin glue-coated collagen patch, fibrin glue, and endobronchial valves. They are usually placed under general anesthesia with an endotracheal tube. An assessment for appropriateness of endobronchial valve placement is performed by a sequential balloon occlusion technique and rarely methylene blue injection. Endoscopic closure of tracheoesophageal fistula is usually a joint effort of pulmonologists and gastroenterologists. Self-expanding metal stents, degradable stents, silicone stents, fibrin glue injections, unidirectional umbrella valves in the bronchi, and congenital heart disease occluders are some of the endoscopic options. Double stenting is usually avoided. Even though deep propofol sedation with high-flow nasal cannula oxygen therapy is possible, at Thomas Jefferson University Hospital, general endotracheal total intravenous anesthesia is preferred.