Acculturation theories and research find that both new culture acquisition and heritage culture attachment are associated with positive outcomes. However, gender-related analyses are rare. In this mixed-method study of 73 Asian Indian American women who were first- or second-generation immigrants from Kerala, India, those classified as behaviorally bicultural, assimilated, separated, or marginalized did not differ significantly in well-being. Being older and married was related to higher self-esteem; unmarried women reported more Kerala attitudinal marginalization. With age, marital status, immigrant generation, and both cultural behavioral orientations controlled, Kerala attitudinal marginalization (but not Anglo attitudinal marginalization) correlated moderately with both lower self-esteem and more severe depressive symptoms. Content analysis of open-ended question data suggested associations among more intricate and multifaceted acculturation processes and psychological well-being via the rewards and challenges the women described. Attaining the "best of both worlds" that some mentioned meant selective adoption and rejection of facets of each culture: family connectedness and control, freedom and moral decline, opportunity, and discrimination. For these women, status-related characteristics (being younger and single representing lower status), discrimination experiences, and attitudinal rejection of their heritage culture (although it accords women lower status than men) had negative psychological outcomes. (PsycInfo Database Record (c) 2020 APA, all rights reserved).