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The transition from Grade 8 to Grade 9 plays a pivotal role in shaping students’ overall high school experience. This study investigates this critical period by examining the academic and social perspectives of students in both grades, along with insights from their teachers and department chairs. By integrating these multiple viewpoints, the study offers a comprehensive understanding of the transition experience, highlighting key discrepancies in students' expectations versus realities of high school, differences between honors and non-honors students, and variations in staff perceptions of course difficulty and rigor. The findings provide actionable insights to help educators and administrators more effectively support students’ academic and social experiences during this important transition.