Life on the street is not a joyride for anyone, but it becomes even more difficult in advanced age, as an individual’s health becomes increasingly fragile and personal social networks disintegrate. Considering the aging of the global population, this somber perspective threatens more and more people, here and elsewhere. The phenomena has been observed in downtown Montreal by researchers, public health providers and workers within community organisations serving the homeless (RAPSIM, 2011, City of Montréal, 2011, ASSSM, 2008). A number of issues have been identified in adapting practices to emerging needs for social integration, healthcare services and housing. We present results from the first phase of exploration from this ongoing research program, followed by preliminary conclusions and analysis of the situation, as well as potential directions for future phases of research.