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Little is known of how homeless and other urban poor populations have fared during the robust economy and within structural changes in health care delivery and entitlement programs of the 1990s. This is important in determining the need for population-specific services during a vigorous economy with low unemployment and increasing Medicaid managed-care penetration. This study compared health insurance status and availability of a source for usual medical care, psychiatric and substance abuse comorbidities, and perceived causes of homelessness in homeless adults surveyed in 1995 and 1997. Cross-sectional, community-based surveys were conducted in 1995 and 1997 at sites frequented by urban homeless adults residing in Pittsburgh, Pennsylvania. Self-reported medical, mental health, and substance abuse comorbidities, health insurance, and source for usual care were measured. Compared to the 388 individuals surveyed in 1995, the 267 homeless adults surveyed in 1997 had more medical comorbidity (56.6% vs. 30.2%, P<.001) and mental health comorbidity (44.9% vs. 36.9%, P=.04) and required more chronic medication (52.1% vs. 30.3%, P<.001). More respondents in 1997 than 1995 reported having no health insurance (41.4% vs. 29.4%, P<.001). While there was no difference in the overall proportion reporting a source for usual care (78.3% in 1997 vs. 80.2% in 1995, P=.55), fewer persons reported use of the emergency department and more persons reported using a shelter-based clinic for usual care in 1997 compared with 1995. These findings suggest more need for medical care among homeless and urban poor persons in 1997 compared with 1995 and support the continued need for outreach and support services despite a vigorous economy.