The purpose of this paper is to share preliminary findings from a grant-funded research project that explores the experiences of higher education and student affairs (HESA) professionals who work with undocumented students. Specifically, we derived our conclusions from the experiences of 10 HESA professionals with advising responsibilities. Utilizing semi-structured qualitative interviews, our findings reveal that undocumented students require advising beyond academic information, highlighting the need for a more holistic, supportive, and equitable approach. Further, through this analysis, we learned that while belongingness is a concept that undocumented students may never experience due to postsecondary immigrant illegality, HESA professionals could actively disrupt the culture of illegality that permeates higher education institutions.