The insider and outsider positions in migration studies have conventionally been approached in terms of ethnic or national belonging. Recently scholars have problematized the essentialist approaches to these roles by arguing for the inclusion of multiple intersecting social locations that are at play in the constitution of researcher positionality. Less attention has been paid, however, on how different ethnicities are constructed and how they can become politicized and depoliticized at particular moments during the research process. This article discusses the fieldwork experiences of two “apparent outsiders” to the studied diaspora community. Drawing from our experiences in multi-sited and comparative fieldwork on the Kurdish diaspora, we argue that rather than taking insider and outsider positions as a starting-point to understand researcher positionality, scholars need to look at particular moments of insiderness and outsiderness to grasp how the researcher’s assumed ethnicity becomes politicized and depoliticized during ethnographic fieldwork.