Web 2.0 tools have introduced a dynamic aspect to learning in contemporary classrooms. Pre-service teachers require expertise in the use of these spaces. The metaphor of outsideness—engaging with distant peers using Web 2.0 tools—has affordances that support the development of this expertise. In this paper, a conceptual framework is outlined that links a model of developing expertise with the affordances of outsideness and a case study of pre-service teacher education is used to demonstrate the framework’s possibilities and limitations. Implications are drawn for the use of online collaborative spaces in higher education.