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Although the HIV/AIDS epidemic in Malaysia has been lingering for over three decades since its first reported case in 1986, due to continuous medical advancement and social awareness, people living with HIV/AIDS now have a longer life span and are able to live a relatively normal life. School-age HIV-positive children can obtain formal education like their peers; however, this is not without challenges, especially in terms of stigma and discrimination. This is where school leadership comes to play its part. The purpose of this research is to explore the leadership characteristics of the headmasters towards students living with HIV/AIDS in schools. This study adopted a qualitative methodology where six headmasters of primary schools in Klang Valley were selected using purposive sampling and interviewed. The interview schedule contained four open-ended questions with an overall purpose of examining the characteristics of the headmasters’ leadership towards students living with HIV/AIDS at the schools. Thirteen leadership characteristics emerged from the analysis: “having knowledge and understanding”, “providing knowledge and creating understanding”, “meticulous”, “pragmatic”, “reliable”, “ethical”, “considerate”, “impartial”, “supportive”, “attentive”, “collegial”, “building collaboration”, and “consulting others”. This research serves as a base for future studies on leadership effectiveness, specifically towards students living with HIV/AIDS, as well as for improving guidelines on managing HIV/AIDS cases in schools.