During Islam Karimov’s presidency in Uzbekistan, between 1991 and 2016, the government had a complex, repressive, and paradoxical relationship with Islam. Widespread persecution, fabricated crimes, and unfair treatment of Muslims were common. Therefore, investigating the relationship between the state and Islam involves significant political risk, which has an intimidating effect on both gatekeepers and participants. Based on the field research I conducted, this paper offers insights about what to expect when conducting research in strictly controlled states like Uzbekistan. Identifying the right gatekeepers who can grant or deny access to research sites, obtaining qualifying permissions, and negotiating and collaborating with gatekeepers are important to gain access to and remain in the relevant research sites for the study. This paper contributes to the literature on conducting qualitative research in authoritarian states. The researcher positionality and their role as an insider or outsider are important parts of such research; however, they also present challenges for researchers. The discussions of reflexivity and the reflexivity of discomfort can guide researchers who face similar challenges in the field. This paper also contributes to the understanding of the importance of considering gatekeeping structures in an effort to advance qualitative research methods and research ethics.