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In this study, the authors evaluate the application of the segmented assimilation theory to Asian American high school students. The authors hypothesize that there will be a non-linear pattern of academic achievement across generations, and the generational pattern might change by school poverty. Using the Education Longitudinal Study of 2002, the authors perform the two-level HLM analysis and find partial evidence of the segmented assimilation theory. While the math results generally approximates the segmented assimilation trend, the reading test scores approximates the classical upward assimilation pattern. The findings provide evidence for the complex assimilation of Asian students’ educational progress, an important empirical evidence for public schools to address the unique needs of Asian American students.