Can AI help me choose a Medicare plan?

Partly. It turns your doctors, prescriptions and budget into a side-by-side comparison of the plans you paste in, but the real prices and networks have to come from Medicare's Plan Finder.

Verdict: Half-bot · AI helps, you finish✓ Tested in Llama 3.3 70B · Oct 1, 2026Written for ChatGPT, Claude or Gemini

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Half-bot

01Why half-bot

  • Comparing premiums, deductibles and drug costs is table work AI does fast.
  • It turns plan jargon like Part D, Medigap and Medicare Advantage into plain English.
  • It can't see current plan networks or drug prices, so the numbers have to come from the plans themselves.
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02The prompt

Replace everything in [BRACKETS] with your own details, then paste it into your AI app.

prompt.txt
You are a Medicare counselor who explains plan choices in plain English. This is not insurance or medical advice.

Me: [AGE, ZIP CODE, ON ORIGINAL MEDICARE OR MEDICARE ADVANTAGE NOW]
Doctors I must keep: [NAMES OR TYPES OF DOCTORS]
My prescriptions: [DRUG NAMES AND DOSES]
Plans I'm comparing: [PASTE EACH PLAN'S NAME, MONTHLY PREMIUM, DEDUCTIBLE, OUT-OF-POCKET MAX AND YEARLY DRUG COST FROM MEDICARE.GOV PLAN FINDER]
What matters most to me: [LOWEST COST, KEEPING MY DOCTORS, TRAVEL, OR DENTAL AND VISION]

Your task: compare the plans I pasted and explain the trade-offs.

Rules:
- MUST use only the plan numbers I pasted. NEVER invent premiums, costs, star ratings or networks.
- MUST show a table with one row per plan: monthly premium, yearly premium, deductible, out-of-pocket max, and my yearly drug cost if I gave it.
- MUST tell me to confirm every doctor and drug with the plan or Medicare Plan Finder before I enroll.
- MUST say this is not insurance advice and that free one-on-one help is available from my State Health Insurance Assistance Program (SHIP).
- If anything is missing, ask me up to 3 short questions first.

Give me, in this order: the comparison table, a plain-English pros and cons list for each plan (no more than 3 bullets each), then a checklist of what to confirm before I enroll.

03Steps

  1. Look up the plans for your ZIP code on Medicare.gov Plan Finder.
  2. Copy each plan's costs into the brackets and paste the prompt into your AI app.
  3. Confirm your doctors and drugs with each plan before you enroll.

04What can go wrong

  • This is not insurance advice; your State Health Insurance Assistance Program (SHIP) gives free one-on-one help.
  • Plan networks and drug prices change every year, so confirm them with the plan before you enroll.

05What to use

Any major AI chat app: ChatGPT, Claude or Gemini. The free tier works.

06Our test run

Llama 3.3 70B · graded by GPT-OSS 120BOct 1, 2026Passed with a catch

Sample input we used: A 67-year-old on Original Medicare in Phoenix who must keep a cardiologist and takes two common prescriptions, comparing two Medicare Advantage plans and a Part D plan with Medigap.

  • Uses only the plan numbers given in the input and invents no premiums, costs, star ratings or networks
  • Shows a table with one row per plan including monthly premium, yearly premium, deductible and out-of-pocket max
  • Tells the user to confirm every doctor and drug with the plan or Medicare Plan Finder before enrolling
  • Says this is not insurance advice and mentions free help from the State Health Insurance Assistance Program (SHIP)
  • Gives the comparison table, then pros and cons for each plan, then a checklist to confirm before enrolling, in that order

What came back (excerpt):

This is not insurance advice. For free, one-on-one help, you can contact your State Health Insurance Assistance Program (SHIP).

Majority of 3 runs; word limits counted in code. All 3 runs listed what to confirm (the cardiologist and both prescriptions) but did not say to confirm it with the plan or Medicare Plan Finder.

One run with an invented sample, checked against the prompt's own rules by a second AI model (word limits counted by code). Your results can differ; how we test.

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