This dissertation focuses on the educational aspirations and expectations of a heterogeneous group of women who were enrolled in, or had graduated from, adult education and literacy programs in Boston, Massachusetts. The research questions guiding the inquiry are: (1) Why do educationally disadvantaged women value education--how are these values transmitted, and what are the social processes through which they are translated into the cultivation of educational aspirations and expectations? (2) What are the broader social processes and institutional arrangements that shape educationally disadvantaged women's educational aspirations and expectations? and (3) How are gender, age, race/ethnicity, and social class implicated in the development of educationally disadvantaged women's non-traditional educational trajectories? Feminist standpoint methodologies are used to analyze the educational life histories of each of the women who participated in the study. Using feminist standpoint theories as the overriding theoretical framework for the study, the dissertation argues that social processes of the transmission of educational values and their translation into the cultivation of educational aspirations and expectations create potential spaces for the practice of resistance to gender, age, racial/ethnic, and social class oppression/subordination, presenting opportunities for educationally disadvantaged women to engage in the political process of struggling to achieve a standpoint. The two primary sources of the transmission of educational values were (1) family socialization processes and (2) work experiences. Within families, mothers and grandmothers transmitted educational values by requiring and enforcing school attendance and by offering active encouragement through explanatory frameworks that conveyed messages about the importance of education to daughters and granddaughters. Haitian, Cape Verdean, and African American women were encouraged to take advantage of educational opportunities that their mothers and grandmothers had not had because of their gender or their race/ethnicity, and Latinas and Irish American women were encouraged to take advantage of educational opportunities that mothers and siblings had relinquished by dropping out of school. The women learned from their work experiences that a U.S. high school diploma or GED was a minimum requirement for obtaining legitimate work opportunities and for gaining access to post-secondary education, which was becoming increasingly necessary to maintain employment. Early schooling provided an important social context for the transmission of educational values. Women whose early schooling was well integrated with family had positive early schooling experiences, and women whose early schooling was poorly integrated with family did not. In the context of their later schooling experiences in adult education and literacy programs, the women translated educational values into educational aspirations and expectations by acquiring self-confidence, by achieving and maintaining various forms of independence, and by accepting family responsibility. Although women who transitioned to college faced the same barriers to persistence as those who did not, those who transitioned focused not on these barriers but on challenges directly related to their schooling, socially and/or academically, describing strategies they had developed for overcoming these challenges. These women adopted the identity of "serious student," which kept them focused on their educational goals. They worked through academic challenges by producing a sustained academic effort that evolved though the cultivation of their educational aspirations: They learned that they could achieve academically if they tried hard enough for long enough. In addition, they developed effective strategies for negotiating the challenges of transition by drawing on social and professional skills they had developed in their adult education and literacy programs as well as through their tenacity and commitment to their educational and occupational/professional goals. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]