Objective: Velopharyngeal insufficiency (VPI) surgery in patients with cleft palate increases the risk for airway obstruction acutely. However, the long-term effects of VPI surgery on airway obstruction are unknown. In this work, we prospectively evaluated patient-reported sleep-related impairment scores as a screening tool for airway obstruction in patients with cleft palate (CP). Methods: Patients with CP > 14 years of age from 2 institutions were prospectively administered the Patient Reported Outcomes Measurement Information Systems sleep-related impairment short form. Patient characteristics, medical, and surgical histories were reviewed. Multivariable linear regression analyses were performed to assess the contribution of independent variables to sleep-related impairment scores. Results: Forty-four patients (mean age 20.5 ± 4.7 years) were included. Twenty-three patients (52.3%) were diagnosed with VPI. Seventeen patients (38.6%) underwent VPI surgery, of whom 14 patients (82.4%) were treated with sphincter pharyngoplasties at a mean age of 7.7 ± 4.1 years. Multivariable linear regression models to control for variables that could influence sleep-related impairment such as body mass index (BMI) ≥25 were developed to evaluate the contribution of VPI and VPI treatment. The diagnosis of VPI (β = .52, P = .004), VPI surgery (β = .48, P = .008), and sphincter pharyngoplasty (β = .47, P = .011) were found to independently predict sleep-related impairment in each of the respective regression models. Conclusions: A history of VPI, any type of VPI surgery, or sphincter pharyngoplasty were separately and independently predictive of patient-reported sleep-related impairment long-term. These data suggest that longitudinal airway obstruction screening in patients with cleft palate and VPI deserves consideration.