This article examines the case of the Winston Society, a short-lived wikispace created by a high school English teacher to foster collaborative knowledge-making and social activism among educators. Through an examination of the wiki, questionnaires, and a focal group interview, this paper describes an examination of reasons the "Winston Society" garnered limited uptake among classroom teachers. Scholarship in new literacy studies is then drawn upon to theorize key issues in the study, including teachers' discomfort with digital epistemologies and the potential of online affinity spaces and social media to mediate teachers' professional development, networking, and political activism. The purpose of this paper is to highlight key issues and tensions in this case that may help educators approach Web 2.0 technologies more strategically in other contexts of teacher education. (Contains 1 figure and 1 table.)