Seven things no AI can know about your Medicare

Part fourteen of Healthcare in Retirement. Same warning as every math piece in this series: I am not an advisor. I am an engineer, so I am looking at the numbers, trying to make sense of them, and sharing my work. Yesterday I argued that the AI assistant most people gave up on is not the one that exists now, and gave you three tests. Today is the other half of that argument, because there is a category of Medicare question that no assistant can answer correctly, however good it gets, and the only thing that separates a careful one from a dangerous one is whether it tells you so. I found seven. Each has a government page that proves the point.

Why does a good AI still get my Medicare wrong?

Because three kinds of Medicare facts are out of its reach, and it is not the tool's fault. The first kind is not public yet: numbers the government publishes on a calendar, and today's date is before the date on the calendar. The second kind is public but lives behind a ZIP code or a state line, so a national answer is wrong for you even when it is right on average. The third kind exists only in your own file: your months without coverage, your doctors, your reason for a special enrollment period. An assistant that searches the live web can handle the first two if it is honest about dates and asks where you live. Nothing on the internet can handle the third. Here is the list.

What is not public yet?

The Part B premium for next year, and with it the Income-Related Monthly Adjustment Amount, the surcharge higher earners pay on top of it. Medicare published the 2026 standard premium of $202.90 in a fact sheet dated November 14, 2025, and the 2027 figure will arrive on about the same schedule. As I write this on September 21, 2026, it does not exist. Neither does next year's plan lineup, as far as you are concerned: the regulation says plans may not market the coming plan year before October 1, and the comparison tool goes live on the same day. So an assistant asked in September which plans you can choose for 2027 is describing this year's list and calling it next year's.

Here is the tell, and it is the most useful thing in this article. One 2027 number is already public. On July 28, 2026, Medicare released the 2027 Part D base beneficiary premium: $41.33, up from $38.99, and the memo shows the arithmetic: $38.99 times 1.06. The 2027 Part B premium is not public. Ask an assistant for both. A careful one gives you $41.33 with the memo, and then says the Part B figure has not been announced. A confident one gives you two numbers in the same tone of voice. The second assistant is not lying to you. It does not know the difference between remembering and looking up, and now you do.

What is public, but not the way you think?

Three things. Medicare Advantage and drug plans are sold county by county, which is why Medicare's own Plan Finder will not show you a single plan until you type a ZIP code. A national answer, "there are lots of $0 premium plans," is true and useless, and a reminder from part three: a plan with no premium of its own still means you pay Part B, and availability varies by county. Second, Medigap rights. Federal law sets a floor of guaranteed-issue situations and states build on it. Nevada gives you an annual birthday-month window to switch, under a law the state's insurance division explains in its AB 250 guidance; Arizona has not enacted an equivalent, which part five of this series covered in detail. Ask an assistant "can I switch Medigap plans without health questions?" and the honest answer begins with "which state?" Third, drug prices. The same plan may charge you one copay at a preferred pharmacy and another at a standard one, because the rule at 42 CFR 423.120(a)(9) allows exactly that. So "what will my prescription cost on this plan" has no answer without the pharmacy, which part nine worked through counter by counter.

What exists only in your own file?

Whether you qualify for a special enrollment period, for one. The list of triggers is in the regulation at 42 CFR 422.62, and every one of them is a fact about you: you moved, your employer coverage ended, your plan is leaving. An assistant can read you the list. It cannot know which line is yours. And then the penalty, which is where the engineer in me wanted a table.

The Part D late enrollment penalty is 1% of the national base beneficiary premium for every full month you went without creditable drug coverage after your window closed, added to your premium for as long as you have Part D. Part four showed that arithmetic for 2026. The base premium changes every year, so the penalty changes every year. Watch what that does to a question an assistant cannot answer from the internet: how many months were you uncovered?

Medicare rounds the result to the nearest ten cents, which is why $7.798 shows as $7.80. Two columns in that table can be filled in today, from a government memo. The fourth cannot, because the Part B penalty is a percentage of a standard premium that will not exist until November. And the first column, your months, is not on the internet at all. An assistant that produces a dollar figure for your penalty without asking about your months, and without telling you which year's base premium it used, has produced a number that looks like arithmetic and is actually a guess dressed up as one.

How do I use this at the keyboard?

Ask the assistant three things before you believe a Medicare number from it. What date is this figure from, and is next year's published yet? Which state and county is this answer for? And what would you need to know about me to be sure? A careful assistant answers all three plainly, and often volunteers them. If it does, you have a research partner, and yesterday's tests will tell you whether it is showing real sources. If it breezes past all three, it is a very well-read stranger with no calendar, no map, and no file on you. Enjoy the conversation. Do not enroll on it.

What a Certified Medicare Planner® does differently

They start with the seven things, because the seven things are the job. They know the fact sheet is dated November and will not quote you a 2027 Part B premium in September. They pull your county's list the morning it goes live and your state's Medigap rules from the state, not from memory. They count your uncovered months from your own records and run the penalty with the right year's base premium, twice, once for this year and once for next. And they read the special enrollment list against your life, not the other way around. Bring them the assistant's answer and the three questions above. That is a better first meeting than most. 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.

Next in Healthcare in Retirement: Medicare itself is now using AI to help decide what it pays for, in Arizona, starting this year. What the program is, what the government promises about the human on the other side of the screen, what the first records show, and a question I have been asking since my first job about whether the manager ever reads the report.

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.

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).