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This study examines how gender intersects with family structure to shape grade retention patterns among Asian American children compared to non-Hispanic Whites. Using American Community Survey data (2008-2023), we investigate whether the established "boy crisis" in education—where boys show greater vulnerability to family disruption than girls—varies across racial/ethnic groups. We find that while family structure significantly impacts retention rates across all groups, with children in single-parent and cohabiting-parent families showing higher retention than those in married-parent families, the magnitude of these differences varies substantially by race/ethnicity and gender. Asian American children, particularly East and South Asians, demonstrate lower overall retention rates than their White counterparts across all family structures. Most notably, the gender gap in retention is more pronounced among White children than among Asian Americans, with White boys in non-traditional families showing particular vulnerability. After controlling for socioeconomic factors and multigenerational coresidence, family structure differences largely disappear for girls across all racial/ethnic groups but persist for boys. This suggests that while socioeconomic resources explain much of the family structure effect for girls, additional mechanisms may be at work for boys. Our findings contribute to understanding how cultural factors and gender norms within Asian American families may moderate the relationship between family structure and educational outcomes, potentially offering insights into protective factors that mitigate educational disadvantages.