The article describes the complexity of researching staff—prisoner relationships ethnographically, and scrutinizes how the complexity linked to the research process may inform an analysis of relationships in prison. I argue that ethnographic research comes with uncertainty and insecurity, because the participation of the researcher, as an informed and involved outsider, requires shifting social engagements in relation to which the researcher constantly has to guard and disguise information and positioning to observe confidentiality and build trust. I demonstrate how the experience of the researcher mirrors and resembles the insecurity and uncertainty that accompanies prison relationships that I characterize as relative. I explain why it is therefore difficult to distinguish between insider and outsider, front and back, public and private, trustful and cautious and friend and enemy, and how this results in a constant guarding and disguising of information and positioning among officers and prisoners. Finally, I argue that while social relativity provides uncertainty and multiple loyalties that contribute to the low trust environment of the prison, it also makes possible the compromises, discretion and flexibility required to ensure a tolerable humane flow of everyday life by providing for management of both personal and social agendas.