This article examines first impressions through a discursive and interactional lens. Until now, social psychologists have studied first impressions in laboratory conditions, in isolation from their natural environment, thus overseeing their discursive roles as devices for managing situated interactional concerns. I examine fragments of text and talk in which individuals spontaneously invoke first impressions of other persons as part of assessment activities in settings where the authenticity of speakers’ stances might be threatened: (1) in activities with inbuilt evaluative components and (2) in sequential contexts where recipients have been withholding affiliation to speakers’ actions. I discuss the relationship between authenticity, as a type of credibility issue related to intersubjective trouble, and the characteristics of first impression assessments, which render them useful for dealing with this specific credibility concern. I identify four features of first impression assessments which make them effective in enhancing authenticity: witness positioning (Potter, 1996, Representing reality: Discourse, rhetoric and social construction, Sage, London), (dis)location in time and space, automaticity, and extreme formulations (Edwards, 2003, Analyzing race talk: Multidisciplinary perspectives on the research interview, Cambridge University Press, New York).