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The Chicago Family Case Management Demonstration was an innovative effort to test the feasibility of providing wraparound supportive services, including work supports, for vulnerable public housing families. This brief explores the employment experiences of Demonstration participants. Surprisingly, despite an extremely difficult labor market, employment increased. Further, the intensive Transitional Jobs program appears to have contributed to these employment gains. Yet, despite increases in employment, the economic situation for most Chicago Housing Authority families remains tenuous. For those who remained unemployed, the Demonstration's services failed to address a multitude of personal and structural barriers to work.