This chapter focuses on how the knowledge and experience of living through the HIV epidemic shape older people’s responses (and fears) about chronic illness and health emergencies such as the COVID-19 pandemic. Using the example of Uganda, we examine the ways in which the particular time people first heard about HIV, or encountered it in their lives as a result of their own HIV diagnosis or a diagnosis within their family or wider community, affects their understanding and perception of ill health and the concerns about the risks HIV continues to pose. We describe how the response to information about an asymptomatic chronic condition (at an early stage of potential disease), or a new illness like COVID-19, may be shaped by the experience of living with HIV or taking care of someone with HIV-related illness in the past. Such experiences shape older people’s understanding of symptoms and expectations of the timeline for the illness development.