We present trends in practice as our experience has grown and report the postoperative morbidity and its associated factors after tracheobronchoplasty. A retrospective cohort study was conducted of 161 patients who underwent tracheobronchoplasty from October 2002 to September 2016. The main outcome was development of a postoperative complication within 30 days of the operation. Postoperative complication events were graded using the Clavien-Dindo system. The study patients were divided into two consecutive cohorts to examine trends in systems of care. Postoperative morbidity was examined using a log-binomial regression model. The cohort consisted of 103 women (64%), with a median age of 58 years (interquartile range, 52 to 66 years). Postoperative morbidity occurred in 75 patients (47%). Severe complications (Clavien-Dindo grade ≥IIIa) occurred in 38 patients (24%), most of which were respiratory in nature, including 27 (17%) with respiratory failure. Median intensive care unit length of stay was 4 days (interquartile range, 3 to 5 days), with a total length of stay of 8 days (interquartile range, 6 to 11 days). In-hospital mortality occurred in 2 patients (1%). Discharge was directly to home in 68% of patients (37% without assistance and 31% with visiting nurse follow-up) and to a rehabilitation facility in 31%. After adjusting for age, sex, race, operative time, and intraoperative blood loss, forced expiratory volume in 1 second was an independent predictor (odds ratio, 0.97; 95% confidence interval, 0.95 to 0.99; p = 0.01) for postoperative morbidity. Despite an arduous hospital course with significant risk of severe complication, patients undergoing tracheobronchoplasty for severe tracheobronchomalacia have low risk of mortality and most are discharged directly to home.