Tracheostomy is indicated for varied reasons and is a relatively safe procedure that can be done with both open and percutaneous methods. However, the procedure is often challenging in cases of distorted neck anatomy. Neck swellings often push the trachea laterally or shield it. Even some gross intrathoracic pathology may shift the trachea from the typical trajectory making it challenging to delineate the course of the trachea. A bedside point-of-care technique having a visual aid that can guide the performer thus appears beneficiary. Fiber-optic assistance for correct puncture and confirmation is known, and light-based techniques have been used for tracheostomies. As fiberscopes are not infrequent in tertiary and even secondary care hospitals, transillumination from a flexible bronchoscope can identify the altered course of the trachea, much like a navigation system, and systematically aid the performer in steering away from the obstacles. We present two cases in two scenarios with tracheal deviation who underwent either open or percutaneous tracheostomy with point-of-care ultrasound and transillumination to delineate the course of the trachea and facilitate difficult tracheostomies safely.