In this article, a selection of emotionally charged situations encountered while conducting an ethnographic research project in a prison in the United Kingdom are outlined and analyzed. With reference to three impressionistic field notes, the researcher's responses to interpersonal challenges, and subsequent attempts at impression management, particularly in relation to maintaining a broadly “neutral” and “credible” status are described. The challenges were experienced in the context of the researcher's position within the hierarchical and gendered nature of prison culture; it is argued that the subsequent subjective feelings of ambivalence are characteristic of the relational uncertainties found within prison settings. Reflecting on the impact of emotionally loaded interpersonal encounters helps to support and enrich the quality of the analysis and research. Furthermore, the learning from this process may help researchers undertaking fieldwork in other closed institutions with similar features and with other vulnerable populations.