There's no doubt that Web 2.0--the social and technological phenomenon that enables users to generate content, interact, and share information across borders--can be a force for good in the world of education. The author's enthusiasm for collaborative Web-based content is tempered, however, by concern about these three challenges: (1) Partners versus Promotion; (2) High Touch versus High Tech; and (3) Filters versus Fountains. Education leaders and policymakers should consider these challenges as they develop policies and practices to integrate the Web into professional practice and student learning. (Contains 1 endnote.)