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Large posterior mediastinal masses may lead threatening complications such as critical tracheobronchial compression. Airway management in these individuals is a challenge and being a lower airway obstruction; rescue strategies are limited. We encountered one such case of a large esophageal mucocele causing extrinsic tracheobronchial compression. We have described the anesthetic management of this case using awake fiber-optic assessment followed by intubation. Close communication with the surgical team, meticulous planning of airway management, and early drainage of the mucocele are the cornerstones of management in such patients.