This study examines interactions surrounding the transmission, enforcement, and assessment of compliance with feeling rules. Using ethnographic data, I investigate how actors within an organization that prepares low‐income black and Latino students to attend elite boarding schools serve as both emotional socializers, transmitting particular feeling rules, and emotional gatekeepers, enforcing and assessing compliance with those rules. I find that it was the interactional process surrounding rule reminders—rather than differences in students' behavioral infractions or in the feeling rules themselves—that was most consequential in shaping evaluations of students' compliance with the program's feeling rules. Gendered patterns in these interactions often resulted in male students being treated as behaviorally deviant and female students being treated as emotionally deviant.