This article explores why K-12 education has not effectively integrated Web 2.0 technologies for teaching critical digital skills, despite their transformative potential. Two primary barriers are identified: (1) educators are constrained by issues of access, lack of instructional support, and restrictions imposed by acceptable use policies and teacher evaluation systems; and (2) there is a dearth of large-scale research on integrating digital technologies into instruction in systematic, thoughtful ways. The article argues that preparing students to be critical digital experts requires rethinking both the institutional structures that constrain teachers and the research agenda that should guide them.