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Insider-outsider debates have little currency in the field of prison ethnography, at least in the UK context which lacks a base in convict criminology. Without disregarding the significant criticism of essentialism which lies at the heart of the insider-outsider dilemma across the social sciences, this paper explores the racialised, gendered and classed dimensions of conducting research with white and black male prisoners at two correctional institutions in the South-East of England. Using prisoners’ interviews discussing identity construction and prisoner social relations, framed by Sykes’ (1958) indigenous model and Jacobs’ (1979) importation model, this paper looks to the authors’ contrasting identities/subject positions along the key axes of difference (race, gender, class). Prisoner interviews are used as case studies to illustrate the complex and contradictory ways in which power relations can be unsettled and recast whilst conducting research with incarcerated men. Previous discussion of the significance of adopting a reflexive position in qualitative research in prisons (Phillips and Earle 2010) has met with constructive resistance (e.g. Crewe 2009; Carlen 2010). In this paper, we address the value, but also the limitations, of using a reflexive approach to go beyond simply the telling of ‘confessional tales’.