Counseling psychologists have long considered person-environment interactions (Gelso & Fretz, 2002). Bronfrenbrenner (1979) proposed an ecological model that broadened psychologists understanding of the multiple ecological contexts on development. The present study examined the role of two main ecological challenges: intergenerational family conflict and racism-related stress on the psychological well-being of Asian American college students (n = 131) attending a large mid-Atlantic university. The findings of this present study support that these two ecological challenges are important to consider in conceptualization of the self-esteem problems, career problems, and interpersonal problems of Asian Americans. Significant relationships between these two ecological challenges and depression or anxiety were not found. Results suggest that racism-related stress contributes additional strain to Asian Americans career problems and self-esteem problems beyond that of culturally-based intergenerational family conflict. A moderation hypothesis also was tested in this study. Collective self-esteem was not found to moderate the relationship between the ecological challenges and psychological well-being. Suggestions for research and practice as well as limitations were presented.