This paper, based on three waves of qualitative data with middle‐income families outside of Philadelphia, explores how families deal with the challenge of financing postsecondary education over time. Because of economic setbacks, these families adopt a variety of financial maneuvers to support their young adult children's postsecondary educational plans. In particular, families are driven to sacrifice familial savings accounts and retirement funds, take on significant student loan burdens, and downgrade children's college plans to cheaper, often less prestigious, options. These results highlight the financial vulnerability of families in the middle of the income distribution and the complicated relationship between family economics and postsecondary educational plans for children.