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This paper summarizes a sub-set of findings from a multi-institutional constructivist case study looking at philanthropy in the lesbian, gay, bisexual, transgender, queer, questioning, and intersex (LGBTQQI) alumni communities. The case study includes interviews and focus groups with advancement officers and LGBTQQI alumni, as well as document analysis from institutions and LGBTQQI alumni groups. For this paper we explore the role of advancement officers in the engagement and solicitation of LGBTQQI alumni. Results of the study reveal both institutional barriers and interest in engaging the LGBTQQI community and the need for continued professional development.