Researchers focusing on diasporic contexts face the difficult task of wearing their “academic hats” while at the same time building meaningful relationships with immigrant communities. This is no more apparent (and important) than with “non-community” (i.e. outsider) researchers. Here diasporic communities, having already experienced the trauma of forced migration, must see the academic researcher as one they can trust and who is invested in their long-term well being. In this paper I address methodological and philosophical concerns related to the insider-outsider researcher distinction and to conducting research as an “outsider.” The principle aims of the paper are to critically examine the distinctions that create and perpetuate the insider-outsider polemic, explore what this polemic “looks like” within diasporic contexts, and consider community-based participatory research as one “vehicle” that might effectively address some of the thorniest problems associated with the insider-outsider distinction.