Technological artefacts loaded with user representations, implicit or explicit, tell us something about the expectations of older people. The provision of technology for older people does not arise from a straightforward relationship between engineers and designers and older users. Against this background, it is reasonable to ask what we can learn from exploring user representations over time. An obvious assumption might be that user representations originating from the 1960s or 1970s are quite different from current user representations. If we consider the extensive technology development that has taken place since then, and the increase in life expectancy, changing lifestyles and changing expectations of later life, it would be reasonable to assume that user representations of older people have changed at the same pace. But have they? This chapter explores representations of older users in technological innovations implemented in home-care and home-help services in Sweden during the period 1960–2018.