As the literature on understanding and addressing <span class=”single_highlight_class”>extremism</span> and terrorism has expanded, there has also emerged a significant methodological literature. As well as providing valuable insight about research design, this literature increasingly addresses practical issues, such as how to gain access to difficult-to-reach populations, how to build trust, and strategies for effective interviewing. There remain however a number of relatively neglected aspects of the research process. In relation to long-term qualitative research – a form of research increasingly recognised as essential to advancing our understanding of radical or <span class=”single_highlight_class”>extremist</span> milieus – one of these concerns the more personal challenges that researchers encounter during and after their time in the field. In this article, we contribute to the emerging discussion on these personal challenges by sharing our own experiences of interviewing and conducting long-term fieldwork in a range of different radical or <span class=”single_highlight_class”>extremist</span> milieus. Specifically, we go beyond observations about the well-discussed pitfall of “going native” and the proffering of coping strategies, to a more frank and difficult but, we believe, helpful conversation about how such research can reconfigure our professional and personal relationships and understandings of our own subjectivity, the emotional challenges and discomfort that this can entail and the insights that this can render.