The concept of masculinities has been central to the analysis of private security as a gendered phenomenon. This research has either focused on the identity constructions and practices of security contractors as men or on masculinity as a theoretical and ideological framework for making sense of security outsourcing. This article aims to overcome this dualism by developing a relational, strategic, and discursive understanding of masculinities and focusing on the gendering strategies that create them. These strategies are identified as masculinization of the market and feminization of the state, feminization and racialization of (some) security work, hypermasculinization as a critical or affirmative discourse, romanticizing the autonomous male bond, and militarization of private security. It is argued that private security as well as critical discourses on it integrate business, humanitarian, and militarized masculinities in a way that ultimately legitimizes masculinism and reconstructs masculinity as a privileged category in international politics.