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Research Aim: This paper provides a longitudinal analysis of interview data from a diverse group of Boston parents, applying an intergenerational lens to financial asset transfers with a specific focus on racial and economic disparities. Grounded in research on persistent racial and gender wealth gaps, the study extends the Leveraging Mobility (LM) study—a unique longitudinal qualitative project following Black and White low- to middle-income parents raising children in the 21st century. The LM study examines families’ financial decision-making processes and the trade-offs made between current needs, long-term security, and opportunities for upward mobility. In this paper, we analyze pathways to retirement security and how parents assess their planning at different life stages, particularly in response to macroeconomic shocks like the Great Recession and the COVID-19 pandemic. We also examine the economic positions of their adult children and the intergenerational flow of family wealth.Background: Extensive quantitative research documents significant racial wealth disparities (Asante-Muhammed et al., 2016; Derenoncourt et al., 2022; Pfeffer & Killewald, 2018; Wolff, 2017). While these data offer valuable insights into trends of stratification and mobility, the role of wealth in the cross-generational processes of social reproduction remains under-explored. Relatively little qualitative research has addressed how race, socioeconomic status, and wealth shape families’ retirement planning and experiences. Furthermore, this study focuses on parents who continue to support their children well into young adulthood—a trend that is increasingly prevalent (Minkin et al., 2024).Data and Methods: The LM study is a unique longitudinal, qualitative investigation into the meaning, decision-making, and impacts of intergenerational wealth transmission. Baseline data were collected in 1998 from low- to middle-income parents of young children. Follow-up interviews were conducted post-Great Recession (2010–2012) as the children approached or completed high school. A third wave of interviews, currently underway, allows us to delve deeper into how families share and accumulate wealth intra- and intergenerationally. Critically, these data reveal how financial decisions relate to outcomes for two generations within the same families over a 25-year period, providing insights into complex trade-offs and retirement planning across nearly three decades.Preliminary Results: Findings underscore how neighborhood context and the flow of wealth from grandparents to parents and adult children contribute to retirement security and economic well-being. Furthermore, the analysis illuminates the decision-making processes regarding wealth sharing across three generations for more affluent families, contrasted with the experiences of families who lack access to intergenerational assets.