This article examines the Medicaid Buy-In program, so named because workers with disabilities “buy into” Medicaid coverage with monthly premiums. In 2006, over 97,000 individuals were enrolled in 32 state Buy-In programs. States have taken different pathways toward the program’s dual objectives: expanding Medicaid coverage to vulnerable populations and promoting employment of working-age adults with disabilities. Analyses indicate that some states appear to have accomplished both objectives, whereas other states have emphasized one over the other. In addition, certain program features (such as higher earned-income limits) contribute to both larger percentages of Buy-In participants who are employed and higher earnings of employed participants.