The confluence of rapid population aging and the overwhelming desire of older adults to age in place begs the question: Do our cities support the health and well-being of aging populations? Using a neighbourhood-by-neighbourhood approach, this macro-scale investigation explores the “double risk” that many older adults live with – the potential of being disadvantaged by socio-demographic risk factors (being older, living alone, low income) and by living in an unsupportive built environment. It is an integration of what we know about supportive built form for older adults and applies this knowledge to Canadian cities, using a spectrum approach to classifying built environments. We found that most older adults with socio-demographic risk factors are living in unsupportive built environments in Canada; however, the distribution between built environments along the spectrum and between municipalities reveals a variegated landscape of double risk. Previous research suggests that unsupportive built environments can be supplemented with services, small-scale improvements in the built environment, and larger-scale retrofitting of neighbourhoods. Since the spatial distribution of vulnerability varies greatly within the 33 Canadian cities analysed, it highlights the need for this kind of inquiry to target age-friendly policy interventions.