This article provides a comparative perspective on homelessness in Canada and New Zealand, with a focus on three urban regions. It seeks to document homeless numbers in the chosen cities, to evaluate the utility of counting the homeless, and to identify common and divergent approaches in homelessness policy. Research involved document analysis, key informant interviews, and participant observation. Literal homelessness is found to be several orders of magnitude higher in the Canadian cities. In one of the Canadian centers, suburban homelessness is emerging as a significant phenomenon. Efforts to count the homeless allow such trends to be tentatively quantified, and inform policymaking. Policy differences between the countries are stark: Canadian cities are seeking to respond to an emergency, which may call for a radical change of approach in the form of "housing first." In New Zealand, a national program of social housing, combined with cultural factors, reduces pressure to act.