In 1995 Australia and the United States made ,in theory, commitments to connect their schools and classrooms to the Internet by the year 2000. Over the next few years, each country used methods of private-public sector collaboration to enact this educational goal. To explore this policy and process scenario, case studies in each country were examined through the lens of NetDay. NetDay is an American-based strategy that incorporates community voluntarism, corporate philanthropy and existing education policy structures to connect classrooms and schools to the Internet. NetDay, among other things, is a combination of corporate, political, community, and media sector efforts combined with technology-driven rhetoric about what is demanded from education at the turn of the millennium. The case studies showed from a comparative perspective that schools using private-public sector collaboration to fund school expenditures need various pillars of support. These supports can include a strong personal and professional philanthropic community, an established or emerging concern about social capital, or a commitment to self-funded models of educational institutions. The research suggests that schools should develop a systemic policy on private-public sector collaboration that reflects its educational goals, managerial ethos and community values. This sense of mission may promote more successful and long-term partnerships. Likewise, larger systems (be they states or districts) may need to create an environment where schools are allowed the capacity to build these relationships not merely induced to change through mandates.