Here’s a scary thought. Millions of seniors are about to pick a Medicare plan by asking a chatbot — and a lot of them are going to get burned.
It’s not hard to see why people are tempted. Medicare is a maze. Medicare officials estimate there are roughly 5,600 Medicare Advantage plans on offer nationwide for 2026, plus a pile of stand-alone drug plans. Get the choice wrong and you can make one of the six big Medicare mistakes that could cost you in retirement.
So when open enrollment starts on Oct. 15, plenty of folks will do the modern thing: Type “which Medicare plan should I pick?” into ChatGPT and hope for the best.
I get the impulse. I’ve spent 35 years watching people drown in this stuff, and I’ve heard plenty of things folks wish they’d known before signing up.
And I’m a big believer in artificial intelligence. I use it all the time. I’ve written before about the money chores these tools handle beautifully.
But handing this particular decision to an AI is a mistake — and it can cost you real money. Here’s why.
1. It’s probably working from last year’s information
Medicare plans reset every year. Premiums change. Drug lists change. Networks change. The plan that was perfect last November might be a lemon this November.
AI chatbots learn from data with a cutoff date. Ask one about 2027 plans and there’s a good chance it’s answering from information that’s months or years out of date.
You’d never shop for this year’s plan using last year’s prices. But that’s essentially what an AI can hand you, without ever warning you it’s doing it.
2. It can’t see the prices that actually matter
The real Medicare prices don’t sit out on the open web. They live inside Medicare’s Plan Finder, and they only appear after you punch in your ZIP code and your exact list of drugs.
A general chatbot can’t get in there. So when it quotes you a cost, it’s estimating — or worse, guessing. On a decision worth thousands of dollars, a guess isn’t good enough.
3. It doesn’t know your drugs or your doctors
Here’s what makes Medicare so personal: The “best” plan depends almost entirely on which medications you take and which doctors you see.
Two neighbors on the same street can need completely different plans. A chatbot answering a generic question doesn’t know your prescriptions, your pharmacy, or whether your cardiologist is in your network.
Leave those details out, and the answer you get back is close to worthless.
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4. Medicare is local, and AI talks in national averages
Plan availability, premiums, and provider networks vary by county — sometimes by ZIP code. What’s true in Miami may be flat wrong in Milwaukee.
AI tends to answer in national generalities. That’s fine for “how does Part D work.” It’s dangerous for “which plan should I buy,” where the right answer can change street by street.
5. It sounds certain even when it’s dead wrong
This is the sneaky one. When a chatbot doesn’t know something, it often doesn’t admit it. It serves up a confident, polished, wrong answer instead — a glitch researchers politely call a hallucination.
A bad tip delivered with total confidence is more dangerous than an obvious guess, because you’re far more likely to act on it. And acting on it here means locking yourself into the wrong coverage for a full year.
Where AI can actually earn its keep
None of this means you should close the chatbot tab. Used as an assistant — not the decider — AI is genuinely useful here.
It’s great at explaining jargon, like the difference between a copay and coinsurance. It can boil a confusing plan document down to plain English. It can build you a checklist of questions to ask before you enroll.
Think of it as a sharp research assistant, not a licensed advisor. It can help you prepare. It shouldn’t pull the trigger.
What to do instead
Start where the real numbers live: the official Medicare Plan Finder at Medicare.gov. Enter your drugs and your ZIP code, and it’ll show you actual costs for actual plans in your area. For more, see these 13 tips for finding your best coverage during open enrollment.
Then get a human in your corner — for free. Every state runs a State Health Insurance Assistance Program, or SHIP, that offers free, one-on-one counseling. These folks don’t earn commissions, so they’ve got no reason to steer you wrong.
That last part matters more than you’d think, because plenty of people in this space do have a reason to push you around — including the scammers draining senior bank accounts every enrollment season.
And if you already have a plan, don’t just set it and forget it. The research on that habit is brutal.
Economists at Yale and MIT who dug into Part D found that only a sliver of seniors — as low as 2% in one year — actually landed on the best plan for them. Most could have trimmed 19% to 33% off their drug costs with a better match.
Jason Abaluck, the Yale economist behind that work, called plan selection “an immensely complicated problem.” He’s right. It’s so complicated he’s suggested it practically demands a sophisticated computer algorithm to solve.
But the general-purpose chatbot sitting in your browser isn’t that algorithm. Not for this.
So let the AI help you understand your options. Then verify the real numbers at Medicare.gov, and let a free SHIP counselor check your work. A year from now, your wallet will thank you.