Peer socialization agents (PSAs; e.g., resident assistants, orientation leaders) are trained to facilitate belonging through formal socialization initiatives. We used secondary qualitative data analysis, in combination with a critical constructivist approach, to explore PSAs' sense of belonging and the contexts in which they experience it through ecological systems theory. Findings demonstrated that PSAs rarely experienced a broad sense of belonging, contrary to prevailing wisdom that links involvement and belonging. PSAs are charged with fostering belonging for others while simultaneously navigating systems that undermine their feelings of belonging. Rather than experiencing widespread feelings of belonging, PSAs often experienced it only in specific microsystems that affirmed their identities and experiences, including student groups, organizations, or affinity spaces. Finally, we highlight implications for research and practice.