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Through an interdisciplinary conceptual lens, this study explores how to support the cross-cultural adaptation of unaccompanied international secondary students (ISS) in Canada from a plurality of perspectives. It employs multiple embedded case study designs with a critical intercultural hermeneutics approach. Participants include six ISS from Brazil, China, Italy, Mexico, and Vietnam, along with their parents, homestay parents, teachers, and agents. Data collection spanned the entire 2022-2023 school year, involving serial interviews, online observations, and document analysis. The findings identify a range of supports recommended by students and their caretakers as crucial for successful adaptation. All ISS caretakers are recommended to engage in regular check-ins with the students, listen to them non-judgmentally, and assist in setting future pathways.