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This study examined how parents, general educators, and special educators perceived their communication relationships over time in supporting students with disabilities. Using multi-year survey data (2017–2022), the Parent-Teacher Relationship Scale II (PTRS-II) and its “Joining” and “Communication-to-Others” subscales were analyzed with mixed-effects and distributional models. Results showed relationships improved after 2017, with parents and special educators rating communication more positively than general educators. Parents of children with disabilities—especially cognitive or multiple disabilities—rated communication preferences higher than those of children without disabilities or with other disabilities. Findings underscore role-based variation, contextual influences, and implications for teacher training and family engagement, particularly during and after the COVID-19 pandemic.