Medicare Open Enrollment 2027: Compare Plans With AI Help
Medicare Open Enrollment runs Oct 15 to Dec 7, 2026. A calm, step-by-step way for seniors to check 2027 plan changes, compare on Plan Finder, and use AI to make a side-by-side table without sharing private details.
Quick answer: Medicare Open Enrollment runs October 15 to December 7, 2026. It's your yearly chance to keep, switch, or drop a Medicare Advantage plan or a Part D drug plan for 2027. Read the Annual Notice of Change your plan mailed you, list your drugs, doses, pharmacies and doctors, then compare plans on the official Medicare Plan Finder at Medicare.gov/plan-compare. An AI app like ChatGPT, Gemini or Copilot can turn your notes into a simple side-by-side table and a list of questions to ask. It should not pick your plan, and it should never see your Medicare Number.
If you're happy with your coverage and nothing important changed, you don't have to do anything. Your plan renews on its own. But plans change every year, so a 30-minute check is worth it.
This is educational content, not insurance, legal, or medical advice. Dates and dollar amounts were checked on Medicare.gov, CMS.gov and KFF on October 30, 2026. Your plan's own documents and Medicare have the final word.
Key dates for 2027 coverage
| Date | What happens |
|---|---|
| By September 30, 2026 | Your plan mails its Annual Notice of Change (what's different next year) |
| October 15 – December 7, 2026 | Open Enrollment: join, switch, or drop a Medicare Advantage or Part D plan, or move between Medicare Advantage and Original Medicare |
| January 1, 2027 | New coverage starts. Changes to your current plan start too |
| January 1 – March 31, 2027 | If you're in a Medicare Advantage plan, you get one more chance to switch to another Medicare Advantage plan or go back to Original Medicare |
The plan has to get your request by December 7. Don't leave it to the last weekend: the free counselors listed below get very busy in late November.
What's different for 2027
- Part D out-of-pocket cap: $2,400. Once your out-of-pocket costs for covered drugs reach $2,400 in 2027 (up from $2,100 in 2026), you pay nothing more for covered Part D drugs for the rest of the year.
- Highest allowed drug deductible: $700 (up from $615). Some plans have a lower deductible or none.
- Stand-alone drug plan premiums vary a lot. CMS projects the average stand-alone Part D premium at about $36 a month. KFF, a health policy research group, found that about 3 in 4 people in stand-alone drug plans without Extra Help would pay a higher premium in 2027 if they change nothing, and no stand-alone drug plan has a $0 premium in 2027. That's the main reason to look this year.
- Medicare Advantage drug premiums are projected to drop on average, but averages don't tell you about your drugs and your doctors. Only a comparison with your own list does.
- 2027 Part B premium: not announced yet as of October 30, 2026. Medicare usually announces it in November.
Step 1: Read your Annual Notice of Change
Your plan mailed an Annual Notice of Change (ANOC) in September. It's often a thick booklet, but the important part is a short table near the front comparing this year with next year. Look for changes to:
- The monthly premium
- The deductible
- Copays or coinsurance for your drugs (a drug can move to a different "tier")
- Whether your drugs are still on the plan's drug list (the formulary)
- Whether your doctors and hospitals are still in network (Medicare Advantage)
AI is good at turning this kind of booklet into plain English. Type or photograph only the comparison table, not the page with your name and member ID.
Prompt to copy: "Here is the 2026 vs 2027 comparison table from my Medicare plan's Annual Notice of Change. I've removed my name and member number. In plain words, what is changing for me next year? List anything that could cost me more, and anything I should double-check with the plan. Don't recommend a plan."
If you shared a photo with an AI app, you can delete it afterward. Here's how to delete AI chat history in the most popular apps.
Step 2: Make your list
Before you compare anything, write down:
- Every prescription: name, dose, and how often you take it. The pill bottles have it.
- Your pharmacies: including mail order if you use it.
- Your doctors and hospitals: especially specialists you'd hate to lose.
- What matters to you: a low premium, predictable copays, keeping a certain doctor, dental or vision, travel outside your area.
You can ask AI to tidy this up for you:
Prompt to copy: "Turn these notes into a neat checklist I can take to a Medicare counselor or use on Medicare Plan Finder. Group it into: prescriptions (name, dose, how often), pharmacies, doctors, and what matters most to me. Notes: [paste your notes, no Medicare Number]"
Step 3: Compare on Medicare Plan Finder
The official tool is Medicare Plan Finder at Medicare.gov/plan-compare. It's free, and it doesn't sell you anything.
- Enter your ZIP code. If you log in with a free Medicare.gov account, your current drugs may already be listed.
- Add your drugs and doses exactly as on the bottle, and pick your pharmacies.
- Sort plans by lowest drug + premium cost. This total for the year matters more than the monthly premium alone.
- Open a few plans and check the deductible, star rating, and, for Medicare Advantage, whether your doctors are in network. Call the doctor's office to confirm. Directories can be out of date.
Step 4: Ask AI to build a side-by-side table
Copy the numbers for your current plan and two or three others from Plan Finder into a note. Use plan names and numbers only. Then:
Prompt to copy: "Make a simple side-by-side table of these Medicare plans with these rows: monthly premium, yearly drug deductible, estimated yearly drug + premium cost, star rating, doctors in network (yes/no), and any notes. Then list 5 questions I should ask before I switch. Use only the numbers I give you and say 'not given' when something is missing. Don't recommend a plan. [paste the plan details]"
Then check every number in the table against Plan Finder or the plan's own papers. AI apps can copy a number wrong or fill a gap with a guess. The table is a thinking aid, not the decision.
If a counselor or family member is helping you, print the table and bring it along.
Questions to ask before you switch
- Are all my drugs covered, at what tier, and do any need prior approval?
- Are my doctors and hospitals in network for all of 2027?
- What's the yearly out-of-pocket maximum (Medicare Advantage), and what would a hospital stay cost me?
- Do the "extra benefits" really fit me? Dental, vision, and grocery cards often have limits and fine print.
- Leaving Medicare Advantage for Original Medicare? In most states, a Medigap insurer can ask health questions and turn you down or charge more if you apply outside your first sign-up window. Ask a SHIP counselor about your state's rules before you drop a plan you depend on.
- Paying for drugs in monthly installments? The Medicare Prescription Payment Plan renews on its own each year, but it ends if you switch plans. Ask your new plan to sign you up again.
Watch for Medicare scams this season
Scam calls spike during Open Enrollment.
- Medicare won't call you to sell a plan or to ask for your Medicare Number. If someone calls about "new Medicare cards," free gifts, or "benefits you're missing," hang up.
- Never give your Medicare Number, Social Security number or bank details to someone who contacted you first. Call 1-800-MEDICARE yourself if you're unsure.
- TV ads with a phone number usually reach a sales agent, not Medicare. That's not a crime, but they may only show you some plans.
- Don't paste your Medicare Number into an AI chat either. See what never to paste into AI.
For phone scams that use a cloned voice of someone you love, see AI voice cloning scams.
Free, unbiased help
- Your local SHIP (State Health Insurance Assistance Program): free one-on-one Medicare counseling. They're not connected to any insurance company. Find yours at shiphelp.org or call 1-877-839-2675. Book early; fall is their busiest time.
- 1-800-MEDICARE (1-800-633-4227), TTY 1-877-486-2048, 24 hours a day, 7 days a week, except some federal holidays. You can also enroll in a plan by phone.
- Help paying costs: Extra Help (for drug costs) and Medicare Savings Programs (for premiums) are worth asking about if money is tight. CMS says only about half of the people who qualify for Medicare Savings Programs are enrolled.
Once you've picked a plan, put the new premium into your retirement budget, and keep an eye on your Medicare Summary Notice or plan statements in the new year.
Frequently asked questions
When is Medicare Open Enrollment for 2027 coverage?
October 15 to December 7, 2026. Changes you make start January 1, 2027. If you're in a Medicare Advantage plan, you can also switch once between January 1 and March 31, 2027.
Do I have to do anything during Medicare Open Enrollment?
No. If you do nothing, your current plan usually renews for 2027. But premiums, drug lists and networks can change, so read your Annual Notice of Change and compare before December 7.
What is the Part D out-of-pocket maximum in 2027?
$2,400. After your out-of-pocket costs for covered drugs reach that amount, you pay nothing for covered Part D drugs for the rest of 2027. The highest deductible a drug plan can charge in 2027 is $700.
Can AI choose the best Medicare plan for me?
No. AI can explain terms, organize your list, and build a side-by-side table from numbers you give it. It can copy numbers wrong and doesn't know your local plans. Compare on Medicare Plan Finder and talk to your SHIP or 1-800-MEDICARE before deciding.
Is it safe to give my Medicare Number to an AI app?
No. Leave out your Medicare Number, Social Security number and member ID. AI only needs plan names, drug names and costs to help you compare.
Where can I get free Medicare help near me?
Your local SHIP gives free, unbiased counseling. Find yours at shiphelp.org or call 1-877-839-2675. You can also call 1-800-MEDICARE (1-800-633-4227) any time.