In the United States, it is permissible to place an undercover police officer in the jail cell with a suspect. This tactical move is rare and launched only for serious crimes, and it takes place before any charges have been filed. This tactic goes under the name of Perkins operations, from the case ruling that if an individual speaks freely to someone whom they believe is a fellow inmate it is allowed to take advantage of their misplaced trust (Illinois v. Perkins, 1990). In this study, we examine 22 Perkins operations, 60 hours of secretly taped interactions in the cells, and we describe and categorize the different approaches and tactics that the undercover officers used. Based on the descriptive analysis, we conceptualize two pathways to information elicitation (direct and relational) and explore the undercover officers’ use of risky interview tactics. The findings suggest that undercover officers use four broader approaches to establish relationships and gather information, and we were able to identify only a few instances of risky tactics in this sample. The relevance of the findings for human intelligence gathering and counterintelligence are discussed.