This study examines changes in the characteristics of the homeless population before and after a period of extended economic expansion (1992-2002). Data from other sources suggest that, during this 10-year period, the size of the overall population of homeless persons may have declined slightly, though not significantly, both in the city studied and nationally. In-depth surveys of representative samples of homeless adults (N = 249 in 1992-94; N = 220 in 2000-2002) revealed significant differences in the composition of the homeless population across the time period, consistent with queuing theory. Persons experiencing homelessness after the expansion appeared to be a more "chronic," less readily employable population than those interviewed at the start of the expansion: Those interviewed after were older, spent more time living on the streets, had more health symptoms, were more likely to have a diagnosis of schizophrenia, and had more restricted social networks and social support. Policy, research, and service provision implications of the findings are discussed.