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Postsecondary transition planning requires a coordinated set of activities across home, school, and work contexts conducted in collaboration with students, families, and educators. For students who receive special education and English learner services, transition planning also includes consideration of students’ language identities, immigration histories, and dual educational programming. Educators’ understanding of these complex and intersecting identities as students navigate the path from high school into adulthood is essential. To explore this, we analyzed interviews with eight secondary educators to better understand their approaches to and perspectives on transition for students receiving special education and English language services. We share evidence of each and discuss implications for researchers and practitioners to support moving towards more culturally sustaining transitions for all students.