Using a qualitative multiple case study research design, the authors investigated the leadership and collaboration strategies of HBCU administrators seeking to drive queer and trans* student inclusion initiatives on their campuses. Further, organizational challenges were examined to make sense of infrastructure elements that needed to be added to these efforts. Analyzed employing the transformational change process (Kezar & Eckel, 2002), three themes were developed: (1) leadership matters, (2) institutional and external collaboration, and (3) institutionalizing on unstable grounds. Implications for future research, theory, practice, and policy are shared at the conclusion of this manuscript.