In Oregon, property tax revolts and school equalization measures have led to increasingly unstable and more non-discretionary public funding for schools. As a result, public schools are turning to private donations to provide both basic and supplemental educational opportunities. Some schools and districts are raising hundreds of thousands of dollars, while others are raising significantly less. This study uses qualitative interviews and the financial data of nonprofit school foundations to analyze how parent roles, district differences, and local policies contribute to efforts to supplement public education with private dollars. Has the increased reliance on private assistance recreated funding inequality that circumvents state efforts to equalize per pupil funding? This study provides a crucial examination of the potential impacts of private donations on funding equality as a result of and through the reproduction of cultural capital. This study not only contributes to the sociological discussion surrounding community differences in fundraising capacity, but also offers districts and foundations a set of issues to consider when making their fundraising decisions.