Orphans in post-conflict settings have unique needs that have not been well-characterized. In post-conflict Liberia, maternal orphans are more likely to be without care than paternal orphans. This study examined the experiences of maternal orphans in Liberia, as they attempted to care for themselves and seek care from others, and the barriers they faced. In-depth interviews were conducted with 75 post-conflict Liberian orphans. We performed a secondary narrative analysis of interview transcripts from all maternal or double orphans (n = 17). We identified similar elements across narratives: traumatic loss, disconnection from family and community, and the desire for a savior. Female high-risk orphans were more likely to have formal substitute caregiving arrangements in which they were living with someone who was a relative or had been selected by a relative. Male orphans more commonly lacked arranged substitute care, but this allowed them to form relationships with substitute caregivers of their choosing. Sex also played a role in the provision of caregiving; substitute care was provided by women. Findings highlighted the syndemic relationship between poverty, violence, transactional sex, trauma, and substance use that traps high-risk Liberian orphans. Interventions are needed to improve access to mental health care, sober communities, housing, and education support. The need to integrate these services into indigenous institutions and address barriers related to stigma is explored.