This paper defines the metaphor of outsideness in relation to web-based interaction. Outsideness is conceived of as a key influence in online academic conversation. In particular, through the sharing of cultural perspectives, asking questions to resolve doubt, and collaborative writing and re-writing as a basis for shaping ideas through reasoning. An analytical framework is proposed and applied to a case study of an international wiki-based project. Key findings are that there is a tension between participants' sense of inside and outside influences, resulting in a complex and challenging working environment. Students require support to develop nuanced questioning and conversational skills, including multi-model forms of representation and communication to enhance language skills.