Three Prompts To Personalize Your Medicare Coverage Using AI

InnovationHealthcareThree Prompts To Personalize Your Medicare Coverage Using AIByEve Cunningham,Contributor.Forbes contributors publish independent expert analyses and insights. Dr. Eve Cunningham is a physician leader in senior and women’s health.Follow AuthorJun 14, 2026, 04:21pm EDTNEW YORK - MAY 15: Two people walk inside a Medicare Services office on the last day for enrollment in the Medicare Part D program.Getty ImagesEvery day, roughly 10,000 Americans turn 65 and become eligible for Medicare. Many will navigate this decision largely alone. In my previous article, I laid out the five questions every person approaching Medicare should ask before choosing between Traditional Medicare and Medicare Advantage. The decision is genuinely complex and there is currently a lack of unbiased digital tools to help people work through this decision in a way that reflects their actual situation. CMS itself has recognized this gap. In February 2026, the agency issued a Request for Information titled “AI Tools for Medicare Experience Modernization,” seeking AI and machine learning platforms capable of providing personalized plan recommendations, conversational AI support and accessible decision support tools to help beneficiaries make informed coverage choices. The federal government is actively looking for solutions. The State Health Insurance Assistance Program, or SHIP, provides free one-on-one counseling in every state — but funding has faced repeated pressure, and in many areas wait times stretch long enough to threaten enrollment deadlines.In the meantime, publicly available AI tools can already help beneficiaries do what CMS is working toward — distilling Medicare.gov’s information into personalized, situation-specific answers through personalized prompts with frontier large language model applications like ChatGPT, Gemini and Claude.When used correctly, they can do something neither a website nor a brochure can — they can take your specific situation and help you fi...