NEW YORK – MAY 15: Two people walk inside a Medicare Services office on the last day for enrollment in the Medicare Part D program.
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Every 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 figure out what the information actually means for you.
The Difference Between Information And Personalized Guidance
Tools like ChatGPT, Claude and Google Gemini are not Medicare counselors. They should not be the final word on any coverage decision. But they are remarkably good at something that is genuinely hard to find elsewhere: taking a body of public information — like everything on Medicare.gov — and applying it to a specific person’s circumstances in plain language.
The critical word is “specific.” Most people open an AI tool and type something like “What’s the difference between Medicare Advantage and traditional Medicare?” They get a technically accurate answer that is, by design, general. It cannot be anything else, because the tool has no idea who is asking.
The fix is to tell it. The clinical details that matter most to drive decision making are not complicated: a general description of your overall health, the importance of continuity with your current providers and any safeguards you need to prepare for significant health events. Add two financial anchors — whether you are on a fixed income and whether you are more worried about high monthly premiums or unpredictable large bills — and you have given the tool enough to stop being a textbook and start being useful.
Three Prompts That Put You At The Center
The following prompts are designed to be copied, adjusted with your own details and pasted into any major AI tool that has access to the Medicare.gov site. Each one is built around the five-question framework from the first article and structured to surface the information most relevant to your situation rather than a generic overview. Always verify any figures the tool returns against Medicare.gov before making a coverage decision, as premiums and cost-sharing amounts change annually.
Prompt 1: Getting Your Bearings
Select your own specifics from the components in brackets — and the response shifts accordingly.
“I am approaching Medicare eligibility and trying to decide between Traditional Medicare and Medicare Advantage. I live in [city, state]. I take [X number] of medications daily, manage [Y number] of chronic conditions and see [Z number] of specialists per year. I am [minimally/moderately/highly] concerned about serious illness. I am on a [fixed/comfortable/generous] income and [more sensitive/less sensitive] to monthly cost. Using only information consistent with what Medicare.gov publishes, explain how Traditional Medicare — with a standard Part B and a Medigap Plan G supplement — compares to a Medicare Advantage plan. Tailor your answer to my situation and flag anything I should verify directly on Medicare.gov before I enroll.”
Prompt 2: When the Medigap Window Has Passed
The six-month Medigap window is not a minor administrative deadline. Missing it can mean permanently higher premiums and fewer coverage options — a lifelong financial consequence for a timing mistake, as Boomer Benefits describes it.
“I am enrolled in Medicare Parts A and B but missed my Medigap open enrollment window. I live in [your state]. I take [X number] of medications, have [Y number] of chronic conditions and see [Z number] of specialists per year. I [am/am not] concerned about serious illness and [am/am not] on a fixed income. What are my realistic options for [limiting out-of-pocket exposure/ensuring comprehensive coverage]? Include whether medical underwriting for Medigap is still worth pursuing, any state-level protections I should check and how to evaluate Medicare Advantage as an alternative. Flag anything to verify on Medicare.gov, including any guaranteed issue rights I may still have.”
Medigap protections vary more by state than almost any other Medicare variable. A handful of states — including Connecticut, Massachusetts, Maine, New York and Washington — have continuous or birthday-rule enrollment protections that may reopen the Medigap window even after the standard period closes. An AI tool will surface those possibilities and flag them for verification.
Prompt 3: Understanding What You’d Pay in a Bad Year
Most Medicare marketing is optimized for the healthy year. This prompt is designed to stress-test both paths against the year things go wrong.
“Help me think through the worst-case annual out-of-pocket costs under each of these two scenarios.
Scenario A: Traditional Medicare Part A and Part B, [with/without] a Medigap Plan G at average monthly cost — [with/without] a standalone Part D plan at the 2026 national average cost.
Scenario B: a Medicare Advantage plan with a $0 supplemental premium, a $4,500 in-network out-of-pocket maximum and an included Part D benefit.
Walk me through the predictable monthly costs, what I’d owe if I needed a hospital stay and the true maximum I could owe in a year under each. Verify the numbers on Medicare.gov.”
The $4,500 out-of-pocket maximum in the prompt is illustrative — the legal in-network ceiling is $9,250 in 2026. Pull the actual amount for any plan under consideration at medicare.gov/plan-compare.
What To Do With The Answers
The output from any of these prompts is a starting point, not a finish line. Use it to sharpen the questions you bring to Medicare.gov’s plan comparison tool, where you can enter your zip code, your medications and your preferred doctors to compare actual plans side by side. If the AI surfaces a state-specific Medigap protection or a guaranteed issue right you were not aware of, take it to your state insurance commissioner’s website or to a SHIP counselor to verify — find one at shiphelp.org.
What AI does well here is compression and personalization: it takes a large body of public information and filters it through the lens of your specific situation in a way that a general website cannot. What it cannot do is access your medical records, confirm whether your doctor is in a specific plan’s network this year or guarantee that the figures it returns are current. Always cross-check on Medicare.gov before enrolling.
The information to make a good Medicare decision has always existed. What has been missing is a way to make it feel like it was written for you. For the 10,000 people aging into this decision today, AI prompting can help navigate the sea of information available.