This paper focuses on the notions of insider and outsider and these positions as they are situated in and out of the established western academic tradition, and the associated ethical, epistemological and methodological concerns, specifically as relates to both our independent and collaborative research "with"("in") Alaska Native Yup'ik communities. The paper begins with a brief discussion of traditional views of the dualistic notion of insider/outsider in ethnographic research, which is juxtaposed with tensions existing between traditional views of insider/outsider and the views of Indigenous ethnographers conducting research among Indigenous populations. Using examples taken from our independent and collaborative research data and transcripts from our Independent Study discussions, we map the paths taken in reconstructing a dualistic view of insider/outsider, western/indigenous, knowledge creator/knowledge receiver. Drawing on Habermas' theory of communicative action, Vygotsky's sociocultural theory of language and learning and Indigenous approaches to decolonising research methodologies, we take first steps to open a dialogue that reconceptualises what it means to participate in collaborative research, working the hyphen with(in) the contact zone. (Contains 2 notes.)