The continued underrepresentation of student affairs Professionals of Color poses an ongoing challenge to fully realize the supposed values of social justice and inclusion in student affairs. Midlevel student affairs administrators provide a unique experiential lens to better understand organizational culture, critique structures, and challenge existing dominant practices. Using narrative inquiry, this study explored the professional and personal experiences of seven racially minoritized midlevel student affairs professionals. Analysis using Ray's Theory of Racialized Organizations reveals ongoing issues of intrapersonal racism and illuminate how institutional structures further contributed to racialization of the participants. Four main themes are identified: racialized middleness, organizational conditions, intrapersonal relationships, and navigating unwritten rules of the field. Findings also draw important considerations for improved practice beyond campus communities. Implications for institutional leaders, graduate preparation programs, and the responsibility White folks must take on are provided. Additional considerations for future research are also discussed.