Context: Emerging research indicates parental educational attainment is not always stable over time, particularly among young adults with lower levels of income and educational attainment. Though increases in postsecondary education are often highlighted as a route to greater earnings among higher-income students, it is unclear whether increases in parental educational attainment can improve the socioeconomic circumstances of low-income families. Objective: The first goal of the current study was to determine whether low-income mothers increased their educational attainment over a 6-year period as their children transitioned from early childhood through elementary school. Second, the current study examined a range of individual characteristics that may help or hinder a mother's re-entrance into education. Last, associations between increased maternal education and indicators of family socioeconomic resources were examined to determine ways that increased education among low-income mothers of young children may serve as a mechanism to reduce poverty or other poverty-related risks. Design and Sample: Data for this study come from the Chicago School Readiness Project (CSRP), a cluster randomized control trial of Head Start centers and a longitudinal follow-up of children and their families. The current study included 432 participants. Of those participants, 97% were the child's mother or female caregiver, 70% lived below the Federal Poverty Line at baseline, and 93% identified as a racial/ethnic minority (i.e., African American, black, or Hispanic). Main Outcome Measures: Maternal educational attainment was collected at 4 time-points across a 6-year period. From these data, a binary variable was created to indicate whether (1) or not (0) mothers increased their educational attainment. Maternal report of household income, unemployment status, and poverty-related risk were examined as indicators of family socioeconomic resources. Results: Thirty-nine percent of mothers increased their educational attainment over the 6-year period of study, and the majority of those mothers attained additional degrees rather than years of schooling alone. Mothers whose children attended treatment-assigned preschool classrooms at baseline were subsequently more likely to increase their educational attainment over time than were mothers of children who initially attended control-assigned classrooms in preschool. Analyses of the roles of parental characteristics in predicting gains in maternal education suggest that mothers who reported greater depressive symptomatology were less likely to increase their educational attainment. Increases in educational attainment, in turn, were positively associated with income earned in subsequent years of our longitudinal follow-up study and negatively associated with maternal unemployment and poverty-related risk when children were in 5th grade. Conclusions: Increases in parent educational attainment were impressive for our sample of low-income mothers, given their exposure to a range of poverty-related risks. Furthermore, our analyses support prior research suggesting that increases in maternal educational attainment may serve as an important mechanism to reduce families' experience of income poverty.