As states expand prerelease and transition services for incarcerated individuals under the Medicaid Reentry Section 1115 Demonstration Opportunity, we sought to systematically inform Medicaid state and plan administrators regarding the population size and burden of disease data available on incarcerated populations in both jails and prisons in the United States. We analyzed data on eligibility criteria for new Medicaid prerelease and transition services based on incarceration length and health conditions across states. We estimated the potentially eligible populations in prisons and jails, considering various incarceration lengths and health status requirements. We also compared disease prevalence in the incarcerated population with that of the existing civilian Medicaid population. We found that rural and smaller states would experience a disproportionately large proportion of their Medicaid populations to be eligible for prerelease and transition services if new Medicaid eligibility rules were broadly applied. Self-reported psychological distress was notably higher among incarcerated individuals compared with those currently on Medicaid. The prevalence rates of previously diagnosed chronic hepatitis C and kidney disease were also much higher in the incarcerated population than the existing civilian Medicaid population. We estimated large volumes of potentially Medicaid-eligible entrants as coverage policy changes take effect over the coming years, particularly impacting smaller and more rural states. Our findings reveal very high disease prevalence rates among the incarcerated population subject to new Medicaid coverage, including specific chronic, infectious, and behavioral health conditions that state Medicaid programs, health plans, and providers may benefit from advanced planning to address.