Velopharyngeal insufficiency (VPI) impacts resonance and articulation and contributes to social difficulties. Nasopharngoscopies (NPs) often inform VPI treatment planning. Using a mixed-model prospective design, this study describes the impact of VPI, NP perceptions, and ratings of pain, discomfort, and cooperation during NP from multiple perspectives. Participants (N = 33) were 7 to 16 years old (mean 8.8 years) with diagnoses primarily of cleft lip and palate (52%) or cleft palate (42%). Mostly mothers (82%) completed measures in English (58%). Patients (52%) reported some teasing related to VPI, with higher parent report of their child being teased (70%). Themes of not being understood, teasing, and negative emotions were described. Coping themes included social support, distraction, and speech therapy. Patients’ Beck Youth Inventories-Second Edition scores were in the average range. Over half of patients and parents reported anxiety about NPs and about a third reported understanding NPs. The Faces Pain Scale-Revised mean of 2.5 ± 3.2 and the Face, Legs, Activity, Cry, Consolability scale mean of 2.5 ± 2.2 were low. Discomfort was most often rated as “a little” by patients (55%), parents (42%), speech-language pathologists (49%), and plastic surgeons (39%). There was concordance across pain and discomfort ratings. High cooperation (61%–72%) was seen across reporters, which was negatively correlated with pain measures. Patient anxiety was related to NP pain and discomfort, suggesting integrating coping for procedural anxiety into the NP preparation might benefit patients. Additionally, negative VPI social experiences should be screened for as part of VPI management.