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• Authors highlight an initiative to reduce tracheostomies for free flap cases. • Tracheostomy rates dropped from 92.6% to 42.7% (411 patients, pre- vs. post-2018) • Post-2018, tracheotomy risk factors included primary site and advanced nodes. • No increase in airway or flap failure complications rates in patients without tracheostomies after initiative began. In 2018, an initiative at the authors’ institution aimed at reducing routine prophylactic tracheostomies for head and neck reconstructions with free flaps was implemented. Discussion between the surgical team and anesthesia about if a tracheostomy should be performed became the standard of care. The safety of this selective approach is assessed. Retrospective review of patients ≥18-years who underwent a free flap for oral or oropharyngeal primaries from 2015 to 2021 at a single centre. Statistical analysis included subgroup analysis of patients pre-vs. post-2018. A total of 411 patients were included. Prophylactic tracheostomy rates decreased from 92.6% to 42.7% pre-2018 to post-2018. There was no significant difference in airway compromise or flap failure rates with non-tracheostomy. Post-2018, variables associated with tracheostomies included oropharynx primaries, advanced clinical nodal disease, and bilateral neck dissection (p < 0.05). On multivariate regression, surgical time (OR 1.182, p < 0.001), anesthetic time (OR 1.165, p < 0.001) and advanced clinical nodes (OR 1.304, p < 0.05) had increased odds of tracheostomy post-2018, while scapula vs. radial forearm free flaps had decreased odds (OR 0.717, p < 0.05). Patients with tracheostomies had longer hospital stays and more observed post-operative complications (p < 0.05). Prophylactic tracheostomies can be safely avoided in select patients undergoing oral and oropharyngeal free flaps, with no difference in airway or flap failure complications. These findings support multidisciplinary discussion between surgical and anesthetic teams regarding the indications for tracheostomies in head and neck cases. Further prospective studies are needed to identify exact criteria for tracheostomies in head and neck reconstructions with free flaps. Level of Evidence: 4.