This article commenting on Greenhow, Robelia, and Hughes (2009) examines the potential strengths and weaknesses of Web 2.0 in supporting student collaborative creativity in light of sociocultural conditions of knowledge creation. Weaknesses and challenges are identified related to the embedded and dispersed representation of community knowledge, weak commitment and support to sustained progress, judging of contributions on the basis of popularity instead of advancement, and the conflict between the chaotic emergent Web and rigidly organized schooling. Discussion is extended to the use of the Web for supporting teacher learning and innovation. Research questions are identified calling for design-based research to advance both pedagogy and technology design.