Save Money · Field guide No. 008 · October 21, 2026

How to Use AI During Medicare Open Enrollment Without Letting It Choose Your Plan

A chatbot is a fine study buddy. It is a poor insurance broker.

Difficulty
15-minute job
Time
About 30 minutes, plus the comparison
Saves
Hours of confusion, and possibly a costly wrong plan
Tools
ChatGPT, Claude or Gemini, plus Medicare's Plan Finder

What happened

Medicare's annual open enrollment opened on October 15 and runs through December 7. It's the window to switch drug plans or move between Original Medicare and Medicare Advantage, and plans' costs and covered drugs can change from year to year.

With AI being pitched as a way to pick a plan, a CPA writing for Money Talks News argues against handing the decision to a chatbot. That's sensible: a chatbot doesn't know which plans are sold in your county, may be working from out-of-date information, and can state a wrong answer with total confidence.

Meanwhile, the scam calls have arrived on schedule. Scripps News reports a flood of calls, texts and emails claiming your benefits are "incomplete" or offering free gifts or new cards. Medicare already has your number and won't call to ask you to confirm it.

What to do

  1. Make your list. Every prescription with its dose, your doctors, and the pharmacy you use. This is the part people skip, and it decides which plan is cheapest.
  2. Have a chatbot turn it into questions. Use the prompt below to get a checklist of what to compare and plain-English definitions of terms like deductible, formulary and network.
  3. Compare on the official tool. Enter your list in Medicare's Plan Finder at medicare.gov/plan-compare, which shows the plans actually sold where you live.
  4. Get a free second opinion. Your State Health Insurance Assistance Program (SHIP) offers free, unbiased counseling. You can also call 1-800-MEDICARE.
  5. Hang up on "Medicare" calls. Don't give your Medicare number to anyone who contacts you first. If you're unsure, call 1-800-MEDICARE yourself.
The prompt

The prompt

I'm comparing Medicare plans during open enrollment. Don't recommend a specific plan. Instead: 1) turn my list below into a checklist of questions to answer for each plan I compare (drug coverage and tier, pharmacy, doctors in network, premiums, deductibles, out-of-pocket maximum); 2) explain in plain English any terms I'll need; 3) list anything important I may have forgotten to include.

My prescriptions and doses: [list]
My doctors: [list, no addresses needed]
My pharmacy: [name or type]
What matters most to me: [e.g., keeping my doctor, lowest total cost]

Leave out your name, Medicare number and date of birth. The chatbot doesn't need them.

Where it still needs a grown-up

  • A chatbot can't see which plans are offered in your area or this year's prices. Treat anything it says about specific plans as a guess and check it on medicare.gov.
  • This is a health and money decision. A SHIP counselor or a licensed adviser should check your choice, especially if you're moving between Original Medicare and Medicare Advantage.
  • Strip personal identifiers before pasting anything into a chatbot.

The verdict

Let the chatbot do the homework. Let Medicare's own tools and a free counselor grade it.

Sources