Part eighteen of Healthcare in Retirement, and the first one that is a how-to. I am not an advisor. I am an engineer who uses an AI assistant all day, and the single most useful thing I do with it is hand it a document and ask it questions. Your plan's Annual Notice of Change is the document of the month; Medicare's mailing guide says "By September 30, people will get a notice from their current plan" about next year's costs and coverage. Part seven read that letter like a spec sheet. Today I want to show you how to read it with an assistant, in the exact words I would type, and then be honest about the three places it will fail.
Can an AI read my plan's Annual Notice of Change for me?
Yes, for everything that is printed on the page, and no, for everything that is not. An assistant with the letter in front of it can find every line that changed, explain what a section means, do the arithmetic on your own visits and prescriptions, and draft the questions you should ask a professional. It cannot know which other plans will be sold in your county next year, whether your doctors are in next year's directory, or what your prescription costs at your pharmacy, because none of that is in the letter. Used for the first list, it is the best reading partner most of us have ever had. Asked the second list, it will guess, unless you have set it up to say "I do not know." This article does both.
What should I never paste into an AI?
Your Medicare Number, your Social Security number, your date of birth, your street address, and the member ID on the plan card. Medicare's own rule for the card is that you share your number only with your doctor "or people you know should have it," in the words of its fraud page, and a chatbot is not on that list. AARP surveyed adults 50 and older in February 2026 and found that 69% "do not feel comfortable sharing their personal health information or medical documents with a health-specific generative AI-powered tool, chatbot, or agent." That instinct is correct. The good news is that the useful part of the letter contains no secrets. The Summary of Important Costs, a table a few pages in, is the same for every member of your plan. The first page may print your name and address, so cover or skip it, and type or photograph the table and the sections you want explained. If you would rather not use your letter at all, Medicare publishes the template every plan builds from, and you can practice on that.
What do I actually type?
Five prompts, in this order, and one sentence before all of them. Start every session with: "Use only the text I paste. If something is not in the text, say so." That one line is the difference between an assistant that reads and an assistant that improvises. Then:
| Step | Type this | What you get |
|---|---|---|
| 1. Find what moved | "Here is the Summary of Important Costs table from my plan's Annual Notice of Change. List every line where the 2027 number differs from the 2026 number. Show both numbers and the difference." | The spec sheet, reduced to the lines that matter |
| 2. Translate a section | "Explain the section called Changes to Part D Drug Coverage in plain English. For each point, quote the exact sentence from my letter you are relying on." | Plain English, with the receipts |
| 3. Run your year | "Using only the numbers in this letter, estimate what changes for a year with eight specialist visits and one daily medication that moved from tier 2 to tier 3. Show the arithmetic line by line." | Your own version of the $524 table from part seven |
| 4. Prepare the meeting | "Write five questions I should ask a Certified Medicare Planner® about this letter, in order of how much money each could involve." | An agenda, so the meeting starts in the middle |
| 5. Find the edges | "List everything in this letter you cannot evaluate without information you do not have, and tell me what that information is." | The list of things that need a human |
Swap your own numbers into step three; eight visits and one tier change are the example from part seven, not a recommendation. Step five is the one people skip and the one I would not. A good assistant answers it with a list that looks a lot like the rest of this article. A poor one says "nothing," and now you know which one you have.
How do I make it show its work?
Ask for the section number and the sentence, every time, the way step two does. The letter makes this easy because every plan builds it from a government template, Medicare's Model Annual Notice of Change, and the sections are numbered. A Medicare Advantage plan with drug coverage uses 1.1 for the premium, 1.2 for the out-of-pocket maximum, 1.3 for the provider network, 1.4 for pharmacies, 1.5 for medical benefits, 1.6 for the drug list, and 1.7 for drug costs. A stand-alone drug plan's letter is shorter: 1.1 for the premium, 1.2 for pharmacies, 1.3 for the drug list, and 1.4 for drug costs. If an assistant tells you something changed and cannot point to the section, it did not come from your letter. The government, for what it is worth, wants this kind of help to exist. In February 2026 Medicare posted a request for information on SAM.gov seeking conversational tools for plan selection, and its reasoning, as reported by Healthcare Innovation's David Raths, was blunt: "Current tools used by CMS rely primarily on static comparison tables and documents that can be difficult to navigate, particularly for beneficiaries with limited health literacy, language barriers, or cognitive challenges." That is the government describing the letter you are holding. Reading it with a tool that quotes its sources is not cheating. It is the intended use.
Where will it still be wrong?
Three places, and you can test all three. First, ask it which other plans in your county will be cheaper next year. The correct answer is that it cannot know, because plans may not market next year's lineup before October 1 and Medicare's comparison tool switches over the same day. An assistant that names plans in September is naming this year's. Second, ask whether your doctor is in the plan next year. On a Medicare Advantage letter, the provider network section says the network changed and tells you to check the 2027 directory, which is a separate document the assistant does not have. Third, ask what your prescription will cost at your pharmacy. The drug cost section gives tiers, not counters, and part nine showed why the counter matters. And one thing from the letter itself that no reading can prevent: the drug list can change during the year, with notice, under the rule part seven walked through. If your assistant gets all three of these right, by admitting it cannot answer them, keep it. That is a research partner. If it answers all three confidently, it just failed the test from part fourteen.
What if the letter says the plan is ending?
Then you are holding a different letter with different rights, and an assistant will not know that unless you tell it. Part six covered the non-renewal letter, the special enrollment period it triggers, and the Medigap door it can open if you move to Original Medicare. If the first page says the plan will not be offered next year, paste that sentence in first, and ask the assistant to read everything else in that light. Then call a human, because that letter has a clock on it.
What a Certified Medicare Planner® does differently
They read the same table you just had the assistant read, and then they read the two documents the assistant did not have: next year's provider directory against your doctors, and next year's plan list for your county the day it goes live. They know your pharmacy. They know which section the surprise is in before they open the letter, because they have opened hundreds. And they are the right person to hand step four to, because a client who arrives with five ranked questions and a page of arithmetic gets a better meeting than one who arrives with a sealed envelope. The advisors are at 602-281-3898.
Friday, October 2. Foothills Library, Glendale, 10:30 AM. Mustang Library, Scottsdale, 2:30 PM. No cost. Register at 123easymedicare.com/medicare-workshop or call (877) 220-1089.
This event is presented by 123EasyMedicare, a brand of American Retirement Advisors, an independent, private organization. It is not sponsored by, endorsed by, or affiliated with Medicare, the Centers for Medicare & Medicaid Services, the Social Security Administration, or any government agency. The libraries are not sponsors of, and are not affiliated with, this event. Educational only; not tax, legal, or insurance advice.
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Disclaimer: This article is for educational purposes only. It is not sponsored, endorsed, or otherwise representative of Medicare or the federal Medicare program. American Retirement Advisors is not a government agency. For official Medicare information, visit medicare.gov or call 1-800-MEDICARE (1-800-633-4227).