The use of psychoactive plants by traditional healers in southern Africa appears to be a neglected area of ethnobotanical research. This article explores the healing dynamics involved in the use of popular psychoactive plant preparations known as ubulawu in the initiation rituals of Southern Bantu diviners. Research methods include a review of the literature, fieldwork interviews with Southern Bantu diviners, and an analysis of experiential accounts from diverse informants on their use of ubulawu. Findings reveal that there is widespread reliance on ubulawu as psychoactive spiritual medicines by the indigenous people of southern Africa to communicate with their ancestral spirits—so as to bring luck, and to treat mental disturbances. In the case of the Southern Bantu diviners, ubulawu used in a ritual initiation process acts as a mnemonic aid and medicine to familiarize the initiates with enhanced states of awareness and related psychospiritual phenomena such as enhanced intuition and dreams of the ancestral spirits, who teach the initiates how to find and use medicinal plants. The progression of the latter phenomena indicates the steady success of the initiates’ own healing integration. Various factors such as psychological attitude and familiarization, correct plant combinations/synergy and a compatible healer-initiate relationship influence ubulawu responsiveness.