This chapter explores the dilemmas encountered due to researcher identity and positionality by drawing upon reflections on fieldwork conducted in Kenya on the radicalization and recruitment of youth for the al-Shabaab terrorist organization. Probing into an array of debates centred on the researcher’s religious identity and the research process, the chapter aims to shed light on the question of how the religious identity or position as a Muslim affected the research process and analysis as well as the researcher’s experiences and understanding of herself. In doing so, the chapter discusses the complexity of locating one’s positions either as an insider or an outsider, or even being in-between, when doing intra-group research and unpacks the linkage between religion, identity and positionality in research related to violent radicalization particularly in terrorism research.