Background: The swapping of a supraglottic airway device or a tracheal tube in anaesthetised adult patients is a challenging procedure because potential complications through hypoxemia and loss of airway may occur, with life-threatening implications. This study aims to evaluate which airway technique offers the highest success rate concerning a secure airway in established supraglottic airway and tracheal tube airway exchange scenarios. Methods: After ethical approval, anaesthesiologists were randomised 1:1 into simulated scenarios: an LTS group (malpositioned laryngeal tube) and a Cuff group (relevant cuff leakage of a placed tracheal tube). After that, both groups completed a common scenario consisting of a partially obstructed tracheal tube lumen in a fixed prone position with a Mayfield clamp. The primary endpoint was a successful tracheal airway exchange within ten minutes after the start of the scenario and before severe hypoxemia (SpO2 < 80%) arose. Secondary endpoints were the evaluation of factors influencing success after 10 min. Results: In total, 60 anaesthesiologists (LTS group n = 30; Cuff group n = 30) with a median experience of 7 years (IQR 4-11) were observed. Within 10 min, a malpositioned laryngeal tube was successfully exchanged by 27/30 (90%) participants, compared to the exchange of a tracheal tube with a relevant cuff leakage by 29/30 (97%; p > 0.05). An airway exchange in an obstructed tube scenario occurred in 22/59 (37%). Loss of airway maintenance showed an obvious association with failure in the common scenario (p = 0.02). Conclusion: The results of this simulation-based study reflect that the exchange of an existing but insufficient airway device in clinical practice is a high-risk procedure. Especially in a fixed prone position, the deliberate evaluation of the existing airway patency and well-conceived airway management in the case of the accidental loss of the airway or obstructed airway access are crucial.