Although most Americans agree that postsecondary education is the clearest path to later financial security, many families have trouble saving money to help their children in this process. This article focuses on the struggles of middle-income families as they attempt to negotiate their daily financial realities with their aspirations for their children’s postsecondary education. In particular, the article examines the discord between the high educational aspirations these middle-income families have for their children and their daily financial constraints. We do so by analyzing in-depth interviews with 31 middle-income families living in the greater Philadelphia area. The middle-income parents in our sample are acutely aware of the importance of college for their children’s upward mobility, and they ideally would like to support their children in this pursuit. However, their current financial insecurity, their lack of government support, and the rising costs of college make preparing for this dream increasingly difficult.