Introduction: Mandibular Distraction Osteogenesis (MDO) is an alternative to tracheostomy and works via lengthening the mandible in order to reduce glossoptosis and airway obstruction. While many patients who undergo mandibular distraction avoid the use of a tracheostomy, some patients will require re-distraction or tracheostomy, often due to recurrence of sleep apnea. This paper explores the potential factors that are associated with MDO failure, defined as requiring re-distraction or tracheostomy over other patients who succeed with the initial procedure. Methods: A retrospective review of all patients who had an obstructed airway, 0 to 18 years of age, and underwent MDO at a single institution from 2008 to 2019 was performed. Fisher’s exact analysis, log-rank analysis, and Kaplan-Meier estimates were used to identify associated factors to failure post-MDO. Results: Forty-five patients satisfied the inclusion criteria, of which 11 patients required re-distraction or tracheostomy post-MDO. Of the parameters assessed, postoperative complications and age >1 month were associated with increased odds of failure (P < .05). Syndromic status trended toward significance as an associated factor (P < .1). Tonsillectomy & adenoidectomy before initial MDO was associated with postoperative complications (P < .05). Conclusion: Our retrospective analysis not only corroborates the results of others in regards to the natural association of postoperative complications and syndromic status with MDO failure, but also suggest that prior tonsillectomy & adenoidectomy, and age at surgery in our series may play a role as well.