Within the landscape of postwar era Detroit, space is vast, but places are hard to find. As people tumble down the side of Maslow's pyramid into abject homelessness, they attempt to anchor themselves in locations that suspend the otherwise situational free fall. This article analyzes how time and space are perceived by people experiencing chronic homelessness and how those individual perceptions are informed by the objective time and space urban environment. We conducted our community-based participatory research into the experiences of chronic homelessness both from perspectives of chronically homeless older adult men and from front-line service providers. Themes that emerged are as follows: (1) temporary permanence, (2) permanent temporariness, and (3) lostness. The article concludes with policy implications regarding the procedures for measuring the extent of homelessness and the needs of those who live it.