Background: There is a notable lack of protocols addressing extubation techniques in transoral robotic surgery (TORS) for obstructive sleep apnea (OSA). Methods: This retrospective cohort study enrolled patients who underwent TORS for OSA between March 2015 and December 2021 and were managed with different extubation approaches. The patients were divided into two groups: high-flow nasal cannula (HFNC) therapy and conventional oxygen therapy. The use of an airway exchange catheter (AEC) was investigated. Results: The application of HFNC use versus conventional oxygen therapy led only to a statistical reduction in extubation time (p = 0.024); length of stay in the intensive care unit (ICU) and the episodes of desaturation below 95% were reduced, but data are non-statistically significant. Similarly, the application of an AEC led to a reduction in extubation time in hours (p = 0.008) and length of stay in the ICU (p = 0.024). Conclusions: In patients with OSA who underwent TORS, the use of an HFNC, with or without an AEC, resulted in a significant reduction in extubation time without major adverse events. Additionally, HFNC utilization may decrease desaturation episodes during extubation. Despite limitations, based on the findings of this preliminary investigation, the combination of an HFNC and an AEC emerges as a promising strategy for enhancing the safety and efficacy of extubation protocols in this patient population.