Objective Tracheostomy is performed for various indications ranging from prolonged ventilation to airway obstruction. Many factors may play a role in the incidence of complications in the immediate post-operative period including patient-related factors. The relationship between obstructive pulmonary diseases and acute post-tracheostomy complications has been incompletely studied. Chronic obstructive pulmonary disease (COPD), obstructive sleep apnea (OSA), and asthma are some of the most common pulmonary pathologies in the United States and given the clinical utility of tracheostomies among these patients, it is important to characterize the risk of acute post-operative complications. Design A retrospective chart review identified tracheostomy patients from January 2017 through December 2018 at an academic cancer center. Medical records were reviewed for the technique used, complications, and contributing patient factors. Post-operative complications were defined as any tracheostomy-related adverse event occurring within 14 days. Patient factors examined included demographics, comorbidities, and body mass index (BMI). Results The most common indication for tracheostomy among the 321 patients that met inclusion criteria was airway obstruction or a head and neck cancer surgical procedure. Obstructive pulmonary pathology (COPD, OSA, asthma) was moderately associated with acute complications in bivariate analysis (13.4% complications, p = 0.039). Among the secondary outcomes measured, radiation was associated with early complications occurring in post-operative days 0-6 (1.1%, p = 0.029). Conclusion Obstructive pulmonary patients may have a higher risk of acute post-tracheostomy complications which is clinically significant when considering the utility of ventilation and tracheostomy in the management of acute respiratory failure secondary to these conditions.