The Medicaid Cliff: Preparing for the 2027 Work Requirements

Ed Hendel, Co-Founder & CEO, Sky Island AI

Below are the slides and sources from Ed Hendel's conference presentations on the Medicaid Cliff. Ed is co-founder and CEO of Sky Island AI, which builds tools to help organizations navigate the 2027 transition. To discuss how your organization is preparing, reach out at ed.hendel@skyislandai.com.

Arizona Rural Health Conference

Flagstaff, AZ · June 2-3, 2026

Slides coming soon
University of Arizona Center for Rural Health

Sources

Brookings Institution, “How would implementing an Arkansas-style work requirement affect Medicaid enrollment?,” 2025. brookings.edu/articles/how-would-implementing-an-arkansas-style-work-requirement-affect-medicaid-enrollment/

Congressional Budget Office (CBO), “Re: Estimated Effects on the Number of Uninsured People in 2034 Resulting From Policies Incorporated Within CBO’s Baseline Projections and H.R. 1, the One Big Beautiful Bill Act,” 2025. cbo.gov/system/files/2025-06/Wyden-Pallone-Neal_Letter_6-4-25.pdf

Health Affairs, “Personalized Telephone Outreach Increased Health Insurance Take-Up For Hard-To-Reach Populations, But Challenges Remain,” 2022. healthaffairs.org/doi/10.1377/hlthaff.2021.01000

JAMA Health Forum, “Effect of Personalized Outreach on Medicaid to Marketplace Coverage Transitions: A Randomized Clinical Trial,” 2022. jamanetwork.com/journals/jama-health-forum/fullarticle/2797464

JAMA Internal Medicine, “Racial and Ethnic Disparities in Medicaid Disenrollment After the End of the COVID-19 Public Health Emergency,” 2024. jamanetwork.com/journals/jamainternalmedicine/fullarticle/2819478

Journal of Immigrant and Minority Health, “Medicaid Redetermination and Renewal Experiences of Limited English Proficient Beneficiaries in Illinois,” 2021. pubmed.ncbi.nlm.nih.gov/33755840/

KFF, “A Closer Look at the Work Requirement Provisions in the 2025 Federal Budget Reconciliation Law,” 2025. kff.org/medicaid/a-closer-look-at-the-work-requirement-provisions-in-the-2025-federal-budget-reconciliation-law/

KFF, “Disability and Technical Issues Were Key Barriers to Meeting Arkansas’ Medicaid Work and Reporting Requirements in 2018,” 2019. kff.org/medicaid/disability-and-technical-issues-were-key-barriers-to-meeting-arkansas-medicaid-work-and-reporting-requirements-in-2018/

KFF, “February State Data for Medicaid Work Requirements in Arkansas,” 2019. kff.org/medicaid/state-data-for-medicaid-work-requirements-in-arkansas/

KFF, “Medicaid Work Requirements in Arkansas: Experience and Perspectives of Enrollees,” 2018. kff.org/medicaid/medicaid-work-requirements-in-arkansas-experience-and-perspectives-of-enrollees/

MACPAC, “Enrollment and Access Barriers for People with Limited English Proficiency,” July 2024. macpac.gov/wp-content/uploads/2024/07/Enrollment-and-Access-Barriers-for-People-with-Limited-English-Proficiency.pdf

MACPAC, “State-Reported Medicaid Unwinding Data Brief Update,” June 2025. macpac.gov/wp-content/uploads/2025/06/State-Reported-Medicaid-Unwinding-Data-Brief-Update.pdf

NBER, “Navigating Medicaid: Experimental Evidence on Administrative Burden and Coverage Loss,” 2025. nber.org/system/files/working_papers/w34191/w34191.pdf

NEJM, “Medicaid Work Requirements — Results from the First Year in Arkansas,” 2019. nejm.org/doi/full/10.1056/NEJMsr1901772

The Virtual Case Manager

Sky Island AI's Virtual Case Manager keeps Medicaid enrollees covered through the 2027 transition, for MCOs, hospitals, health systems, and FQHCs.

Learn more