Drill instructors (DIs) are responsible for executing their Services' recruit training programs and for training recruits. DIs assume a variety of roles, including teaching and developing practical skills and knowledge, mentoring, modeling appropriate behavior and attitudes, motivating recruits for success during and after recruit training, applying and instilling discipline, and ensuring the safety and welfare of recruits. This article examines two major research questions at the intersection of gender, gender-integrated training, and the DI role: (1) What differences exist in how DIs experience their role by gender? and (2) how does gender-integrated recruit training affect DIs' approach to training? This article draws from 87 semistructured interviews conducted with Service leaders, training cadre, and DIs in service of a broader Marine Corps interdisciplinary study on gender integration at recruit training. Interviews were conducted virtually and in-person with Marine Corps, Army, Navy, Air Force, and Coast Guard personnel from June to November 2021. Each interview was coded with initial and secondary codes developed through a flexible coding approach. Data were analyzed across and within relevant categories such as gender and Service to identify themes and patterns. Although the DI role was universally described as demanding and difficult, unique challenges for women consistently emerged from the data. The top reported challenges faced by female DIs were personnel shortages, work and family conflict, culture-driven sexism in the training environment from male peers and recruits, and pressure to excel above and beyond their male peers. In recruit training, DIs are responsible for executing gender-integrated practices. Service leaders, training cadre, and DIs described how gender integration practices affect their approach to the role and implementation of training, including addressing and dismantling sexism, shutting down recruit romantic relationships, training all recruits in an equal manner, knowing gender-specific grooming standards, increasing communication among DIs, and working with mixed-gender DI teams. Female DIs face additional challenges in and outside the role compared with their male peers, and some of these challenges are preventable. Staffing and personnel issues plague the female DI population and are a persistent and pervasive challenge to gender integration efforts. Women are a necessary and highly desirable population to fill the DI role, particularly as Services aim to expose recruits to leaders of both genders during their critical first training experience. DIs play an important role in ensuring the successful completion of recruit training, ultimately helping to build the future leaders of the military. The success of gender integration efforts depends on DIs' intentional approach to the process. Future research can build on this work by expanding the scope to other military training environments (beyond recruit training) and examining how DIs' own sociodemographic positions (e.g., gender, race, ethnicity, and sexual orientation) inform their perspective on and approach to equity in the training environment.