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Discourses on later life housing and care are polarized. Ageing in place—most commonly in one’s long-term dwelling—is often presented as the most desirable living arrangement, while moving to a congregate environment tends to be regarded as a last resort. Such polarized discourses can obscure older people’s experiences as they contemplate needs for housing, health, and social care. To expand current understandings of mobility intentions, this paper examines the time work undertaken by older people with chronic health conditions and disabilities to navigate present and future support arrangements. Based on an interpretive analysis of qualitative interviews with 22 older persons receiving home care in Ontario, Canada, I identify three themes that highlight the temporal aspects of mobility intentions: (a) maintaining continuity with the past and present, (b) constructing alternative futures, and (c) facing precarity. Focusing on time work gives insight into the ways people make sense of ageing in place and/or relocating not only in relation to their physical, social, and psychological capacities, but also in relation to perceptions of the past, present, and future. Time work, moreover, has implications for feelings of security in the present and a sense of control over the future. Based on these findings, I make suggestions for developing a comprehensive continuum of supports, so all older people can make meaningful choices concerning housing and care.