Using a constructivist case-study analysis, we explore philanthropy toward higher education among lesbian, gay, bisexual, transgender, and queer (LGBTQ) alumni, examining the role of advancement staff and alumni advocates in engaging LGBTQ alumni to promote individual and community uplift. Data come from focus groups with 37 advancement staff and 23 LGBTQ alumni at three higher education institutions. Findings reveal the importance of advancement staff and alumni in promoting LGBTQ alumni philanthropy. Specifically, participants discussed LGBTQ advancement staff, accounts of microaggressions and overt discrimination, and taking a leadership role in promoting culturally sensitive practices. Both advancement staff and alumni spoke of how alumni volunteering can lead to deeper engagement, and in the difficulty of recruiting and retaining volunteer leaders within the LGBTQ communities. We draw implications from our findings, discussing the importance of relationships and trust when working with alumni from diverse communities. Our discussion also highlights the need to hire a diverse representation of staff, create a warm campus climate for current students, and have culturally competent staff.