Objectives Acquired upper airway stenosis is usually associated with a complex of pathological conditions at the high tracheal and the subglottic levels. Reported reconstructive techniques include widening by incorporation of grafts, segmental resection, and anastomosis or combined procedures. The management of recurrent stenosis after reconstructive surgery is a major challenge and has rarely been discussed in the literature. The purposes of the present study are to compare the clinical course of primary versus revised reconstructive procedures and to analyze the effect of age, diabetes, chronic lung disease, grading of stenosis, extent of resection, and revised procedures on the operative rate of success. Study Design A cohort study in a tertiary referral medical center. Methods The clinical course of 23 consecutive patients undergoing laryngotracheal anastomosis was studied comparing a group of 13 primary with 10 revision procedures. Seventeen patients underwent cricotracheal and six patients thyrotracheal anastomoses. All patients but one were tracheotomized before the definitive reconstructive procedure. Suprahyoid release was routinely performed except for two cases, and only one patient required sternotomy. The Wilcoxon test was used to examine the relationship between preoperative clinical parameters and the postoperative success (i.e., airway patency). Results Twenty-two of 23 patients (95.6%) had successful decannulation. Four patients required a revision procedure because of repeat stenosis at the site of the anastomosis (2) or distal tracheal malacia (2). Residual airway stenosis of less than 50% was noted in six patients, although only three complained of dyspnea during daily-activity exertion. There was no associated mortality. Complications included subcutaneous emphysema (4), granulation tissue formation (3), pneumonia (2), cardiac arrhythmia (2), and one each of pneumomediastinum, neck hematoma, and urosepsis. Protracted aspirations were noted in one patient who had revision surgery. Age was the only parameter that correlated with postoperative airway patency (P