Tracheal injuries are one of the potentially fatal complications following laryngopharyngeal and esophageal surgeries. The patient developed tracheal rent during laryngopharyngoesophagectomy. The injury was diagnosed intraoperative and repaired. However, it did not heal, and the patient developed tracheopleural fistula. Right thoracotomy and latissimus dorsi flap was done under general anesthesia. Postsurgery, the patient was shifted to intensive care unit (ICU), where he developed respiratory distress not improving, with increasing oxygen flows. To avoid damage to the repair, under bronchoscopic guidance bilateral selective mainstem bronchial intubations were done using cuffed 5.0 mm regular endotracheal tubes (ETTs), and ventilation was supported on pressure control ventilation mode. The ventilator support was weaned off to pressure support ventilation mode on postoperative day (POD) 1. On POD2, ETTs were removed under bronchoscopic guidance and were replaced by 7 mm ID long and adjustable flange tracheostomy tube with the tip just above the carina. The cuff was kept deflated, and oxygen with the high flow was provided through a tracheostomy. The high flow was weaned off after 5 days. Later, the patient was managed conservatively by regular chest physiotherapy, antibiotics, bronchoscopic pulmonary toileting, nebulizations, and appropriate antimicrobial therapy. Patient was discharged in stable condition from ICU and hospital.