Scholarship on assimilation and health among Asian Americans in the United States has largely focused on the foreign-born population. As a result, relatively less is known about generational disparities in health among Asian Americans as well as the mechanisms that underlie them. In recognition of such gaps in existing literature, I use the 2016 National Asian American Survey (NAAS) (n=4,242) and first examine how Asian/American identity centrality moderates the relationship between generational status and self-rated health among Asian American adults. In the process, I consider gender as a key modifier in recognition of gendered contexts of migration. I find that Asian identity centrality operates as a health-protective resource among foreign-born first-generation immigrants, in contrast to their native-born counterparts among whom it functions as a risk factor. American identity centrality is also a risk to health, but specifically among second-generation women. Then I use the same data and analyze how discrimination shapes self-rated health across generations, also accounting for differences by gender. I find that second-generation men are most vulnerable to the adverse relationship between discrimination and health, illuminating the contexts of gendered racism as well as generational differences in internalized racism. Lastly, I draw on data from the 2011-2020 California Health Interview Survey (CHIS) and investigate the interrelationship between nativity, ethnicity, gender, and self-rated health among Asian American adults (n=16,754). I find that nativity disparities in health are differentially shaped by the intersection of ethnicity and gender, highlighting the need to consider varying modes of incorporation across Asian ethnic groups in tandem with gendered contexts of migration. Future research should continue to develop a comparative understanding of generational disparities in health among Asian Americans, with greater attention to gender specificity and intervening mechanisms.