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Insider-outsider methodological debates have a long-standing presence in the social sciences. Numerous scholars have analyzed the dynamics of insider-outsider status in qualitative and ethnographic field research. Yet, relatively few have empirically shown how social class background shapes insider-outsider dynamics in the field. Drawing upon in-depth interviews with thirty-five welfare impoverish white women living in the Greater Boston Area, in this paper I examine how cultural capital shaped my access to and rapport with white women on welfare. I demonstrated cultural capital through three key indicators — knowledge of local welfare services, social geographies of race and place, and accurate usage of dialect and mannerisms. Although my usage of cultural literacy gained “insider” status among most of my respondents, other aspects of my identity provided salient differences and resulted in ruptures to building or maintaining rapport. Finally, I discuss the larger methodological implications of insider-outsider status within ethnographic and qualitative research.