Low educational attainment, often a lack of a high school diploma or matriculation degree, has been linked to negative health outcomes and lower quality of life for sexual and gender minorities globally. However, optimism and resiliency have been demonstrated to provide buffering effects on school dropout. We conducted a study in a South African rural setting to understand the school experiences of gay men, drag queens, and transgender women in Mpumalanga, South Africa. We recruited 35 HIV-positive participants using a purposive sampling method and then conducted a series of focus group discussions. A semi-structured focus group protocol was used, which covered three main domains: educational attainment and goals, experiences as a gender or sexual minority in school before matriculation, and personal and social values placed on education. Through a constant comparison analytical approach, we identified four themes to include school violence and discrimination, dropping out or staying silent to cope, competition between drag queens and girls, and education is social power. Our study suggests that sexual and gender minority youth navigate harassment and discrimination, which negatively impacts their educational attainment, but there is opportunity to support their academic achievement and leadership in society by building upon their acts of resiliency.