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Based on data from a longitudinal qualitative study of middle income families in a suburb of a large Northeastern city (N=26), this paper illustrates the multigenerational struggle of financing postsecondary education. At the third wave we find that, similar to earlier waves, most families considered postsecondary education a necessity for their children and were committed to offering substantial financial support towards this goal. While some parents absorbed all or nearly all of the financial burden for postsecondary schooling, others were able to provide limited financial help or non-financial help to the cause. Most parents offered a moderate level of support for postsecondary education, wherein they shared the cost with their children. Across these cases, parents’ own precarious financial situations necessitated a patchwork of strategies to pay their children’s schooling, such as student and parental loans, additional jobs, help from extended family, and the direction of children towards less expensive school options. Despite their considerable economic investments, many parents nevertheless expressed feelings of skepticism towards postsecondary education and questioned whether their efforts would secure a more stable future for their children.