In this discourse analytic article, I discuss the shifting challenges of HIV/AIDS caregiving, as highlighted in previous research, as well as the similarities between past and present challenges as illustrated by the discourses of HIV/AIDS caregivers at a nonprofit organization in South Africa. Using data from interviews with staff members and volunteers, I illustrate how both past and contemporary challenges in HIV/AIDS caregiving relate to an inability to exercise control. Participants’ discourses revealed a contrast whereby, on one hand, they conveyed a sense of being in control over HIV, while, contradictorily, their accounts contained instances of lack or loss of control. I discuss the implications of barriers to control in HIV/AIDS caregiving and the role of communication and interaction research. I conclude by endorsing ongoing, regular assessments of the needs of those undertaking such work in order to identify their evolving needs in light of evolving challenges.