African mourning of loss of lives in South Africa has been shaped by discursive practices of both traditional African cultures and the sociopolitical developments under apartheid and in post-apartheid South Africa. This article reports on changes in mourning practices on the basis of a literature review and uses a collection of examples to highlight the navigation of some cultural and gendered issues relating to mourning, against the backdrop of the everyday experiences of loss of life in South Africa due to violence and HIV/AIDS. The article draws on African womanist and feminist scholarship and focuses on the intersections between cultural and gender practices of bereavement in the lives of professional urban African women. The authors argue for the use of positioning theory and witnessing practices to honor and story the ongoing struggle of African women as these women take different agentic positions by accepting, questioning, resisting, and/or changing cultural mourning practices while they compassionately witness the self and others in the narratives they live.