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, the Tucson-based company that developed the Virtual Case Manager, an AI call center that proactively helps Medicaid enrollees navigate the upcoming work requirements. Read our briefing (PDF) for more information about the Medicaid Cliff. To discuss how your organization is preparing, reach out at ed.hendel@skyislandai.com.
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.
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