This study investigated the gender dynamics of living in child-headed households (CHHs) in a rural area in Swaziland that experiences high levels of drought, poverty and HIV and AIDS. Using a qualitative research methodology, the study examined ways in which children in CHHs meet their daily family needs and address their vulnerabilities according to their gender, focusing on the experiences of the children. The study sample consisted of 10 households, with 5 boy and 5 girl-headed households from the chiefdoms within the area. A semi-structured interview guide was used to conduct interviews in the respondents' own homes. The study focused on the gendered coping strategies used by the children to sustain their household welfare. Three factors were examined: leadership, food provision and education. The findings show that birth order conferred headship or leadership to the eldest sibling irrespective of their gender. Variations in the performance of the three factors, which were influenced by the gender of the household head, were observed. Generally, the children acted in accordance with their socio-cultural norms demanded in fulfilling the role of leadership and food provision. Boy-headed households become disadvantaged because of the boys' reluctance to take tasks which would contravene traditional Swazi notions of masculinity. This was exacerbated by societal expectations of the independence of boys. Hegemonic masculinity puts boys at a disadvantage when societal expectations require them to enact their masculinity through independence, rather than by drawing on the support of their neighbours/family/social networks. However, girls conformed to traditional Swazi norms. Societal compassion with the vulnerability of girls produced sustainable social arrangements and fostered resilience in girl-headed households.