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This study identifies factors predicting health insurance coverage of TANF recipients leaving Medicaid programs. A sample of 785 Medicaid spells of enrollment by able-bodied, non-elderly adults is drawn from a national survey. Employing event history analysis and multinomial logistic regression, the study finds that those who left Medicaid were three times more likely to become uninsured than to become privately insured. Recipients leaving TANF were 24 times more likely to leave Medicaid than to remain on Medicaid. The impact of leaving TANF upon becoming uninsured was moderated by restrictive TANF policies. Recipients who were White and employed part-time were 41–42% more likely to become uninsured than were their counterparts. A high unemployment rate increased a recipient's chance of becoming uninsured by 27.5%. Married people, African Americans, those with full-time jobs, and those with earnings above the poverty line were at least 32% more likely to acquire private coverage than their respective counterparts.