Previous research has recognized the positive impact of participating in high school gay-straight alliances (GSAs) on the psychosocial adjustment of LGBTQ students. Research suggests GSA advisors are in a position to facilitate learning, social support, and psychosocial well-being for students. As student-led groups, past studies have focused on the perspectives and outcomes of students while the roles of advisors remain unclear. The barriers to GSA development have been explored; however, there is no current study that examines how advisors navigate barriers and facilitators of their environment in order to support students toward achieving their GSA’s purpose. The purpose of this dissertation study was to better understand how GSA advisors fulfill their roles. Specifically, the current study sought to identify how GSA advisors perceive missions of GSAs, the obstacles they must navigate, and facilitators that help support their roles. This qualitative case study recruited four GSA advisors from a single school district. Data included semi-structured interviews and documents which were coded, categorized, and themed in response to the research questions. Results suggest advisors perceive their GSA’s mission by understanding the framework of the GSA, the roles of students, and the roles of advisors. Barriers advisors overcome include supporting students regardless of parental approval, effectively navigating school policy, supporting the development of students’ skills, and helping students clarify their GSA’s mission. Facilitators include aligning with supportive administrators, relying on colleagues as co-sponsors, utilizing outside resources from advocacy groups, and supporting transitions of student leadership in order to maintain the existence of the group.