Based on ethnographic research in Iran among the country's Islamic Revolutionary Guards Corps (IRGC) and its Basij militia, this article explores the process of gaining access to these militarized groups in order to conduct long-term research. Specifically, what does it mean to build rapport and gain trust within a highly securitized space such as this? What happens when the researcher is a potential “national security” threat in both Iran and the United States? How is national security enacted in everyday interactions in the field? Given that anthropologists have tended to have an affinity with the group and community they work with, this article explores the implications of research among a group of men in charge of surveillance, intelligence gathering, and citizen suppression in the country. The article argues that in the midst of national security rhetoric, interrogative surveillance is a strategic tool that makes space for engagement.