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22 Medicare Enrollment Checks Before Next Year's Coverage Starts

The plan changes letter, your pill bottles and one free counselor: everything to check before your 2027 Medicare coverage begins on January 1.

By Peter Byalik, Food & Home Editor
Updated · 19 min read

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The most useful check of all needs only the pill bottles from your bathroom shelf and one free government website.

Most people on Medicare don't compare plans at all during open enrollment. It feels like too much, so the envelope goes in a drawer and the plan quietly renews.

That's a sensible reaction to a confusing system, and it can still cost you. Women are 55% of people on Medicare, and more than a third of them live alone. Often nobody else is opening that mail either.

Open enrollment is already underway. It closes December 7, and whatever you choose, or don't, starts January 1. You don't need to read every page that came. You need a handful of specific answers, and most of them take one phone call.

Start with the mail

Your plan sent at least two things this fall, and Social Security may have sent one more. Each has one job.

22The plan changes letter you put away

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The envelope from your plan that showed up around the end of September has an official name, the Annual Notice of Change. Plans have to mail it by September 30. Most people call it the plan changes letter, and plenty of them never open it.

It's the one place your plan has to spell out what it costs and covers this year next to what it will cost and cover starting January 1. Nothing else in your mailbox this fall does that.

You don't have to read all of it. Near the front there's a summary table with two columns, this year and next. Go row by row: premium, deductibles, copays, out-of-pocket max. Put a pen mark beside any row where the numbers don't match.

Can't find it? Call the member services number on the back of your plan card and ask for another copy, or look under plan documents on your plan's website. Then get the pen out.

21The thick booklet that came after it

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By October 15, your plan also had to send or post its Evidence of Coverage. It's the full rulebook for next year, and it's thick enough to prop a door open.

Nobody reads it cover to cover. Use the index for three lookups instead.

1. Prior authorization. That's when the plan has to say yes before you get a test, a scan or a drug. Look up anything you had done this year.

2. Referrals. Find out whether you'll need your primary care doctor's okay to see a specialist in 2027.

3. The thing you use most. Physical therapy, a home oxygen supplier, dental cleanings, hearing aids. Look it up by name and read what it says about limits.

Write those three page numbers on the cover. If a phone rep tells you something different in March, you'll know exactly where to point.

20A single letter saying your plan is ending

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What if my plan is going away and I threw out the only warning?

It happens. Insurers drop plans because of cost, low enrollment or poor quality ratings, and they only have to send one cancellation notice. If it looked like every other window envelope, it may be in the recycling bin.

A plan you've had for years is not guaranteed to come back.

If no plan changes letter came this fall, that alone is worth a call. Phone member services and ask one question: "Is my plan being offered in 2027?"

If the answer is no, don't wait to see what happens in January. Call 1-800-MEDICARE (800-633-4227) and say, "My plan isn't renewing. What are my options, and what's my deadline?"

19Any notice asking you to confirm something

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When you join a new plan, the insurer sometimes writes back asking you to confirm information before the enrollment goes through. If nobody answers, the application can be turned down. By the time you find out, open enrollment may be over, which is a frightening spot if you rely on an expensive drug.

One phone call protects you. About a week after you enroll, call the new plan and say: "I enrolled on [date]. Is my enrollment complete, or do you need anything else from me?"

Then make sure Social Security has your current address. Medicare uses the address Social Security has on file. A move or a new PO box that never got updated is a quick fix by phone or through your online Social Security account.

In a post office box, plan mail looks like every other envelope in there. A request for one missing detail can sit unopened for weeks.

See more: 29 Conversations Families Keep Putting Off Until It's Too Late →

18The income surcharge on your Medicare premium

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This surcharge is set from an old tax return, so it can lag behind two big changes: a spouse's death and retiring from a paycheck. If either happened in the last couple of years, this one deserves a gentle look.

Some people pay more than the standard Part B and drug plan premiums because of their income. That extra charge is called IRMAA, short for income-related monthly adjustment amount. It's set from your tax return two years back, so 2027 premiums are based on your 2025 return.

For a widow, that can mean being billed as though two incomes were still coming in. Something similar happens to a woman whose paycheck stopped when she retired.

You can ask Social Security to use your current income instead, with Form SSA-44. The death of a spouse counts as a life-changing event, and so does stopping work. For a death, a copy of the death certificate is the proof.

There's no fee, and you can file any time after the event. If Social Security says no, you have 60 days to ask it to reconsider.

What next year will cost you

The premium is the number everyone checks first. On its own, it tells you the least.

17Next year's premium next to next year's copays

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A premium that went down looks like good news, and sometimes it is.

But a lower premium can come with higher costs when you actually use care, and a higher premium can buy lower ones. The changes each year go well beyond the monthly bill, into copays, coinsurance (your share as a percentage) and what's covered at all.

Here's a test using your real year. Count your visits since January: primary care, specialists, any urgent care trip, any scans or lab work. Price that same year using the new copays in the letter.

Add twelve months of next year's premium. Then do the same sum with this year's numbers. If the total went up, the lower premium wasn't the deal it looked like.

Your pharmacy receipts and the appointment reminders on your phone hold most of what you need.

16Your Advantage plan's out-of-pocket max for 2027

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If you're in Medicare Advantage, find one number in your letter: the out-of-pocket max. It's the most you'd pay in a year for covered care before the plan pays the rest.

The federal ceiling rises in 2027. Plans can set the in-network limit close to $10,000, and the combined in-network and out-of-network limit close to $15,000. Some plans set theirs lower.

This is the number to weigh most if you have a knee replacement coming, a cancer follow-up schedule, or a heart condition that puts you in the hospital now and then. In a quiet year, you'll never touch it. In a hard year, it's your real price.

See more: 24 Aging-in-Place Renovations Worth the Money →

15The new drug deductible and yearly drug cap

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Two drug numbers change on January 1, and both go up.

The deductible, what you pay before drug coverage kicks in, can be as high as roughly $700 in 2027, up from about $600.

The yearly cap on what you pay for covered drugs rises to about $2,400, up from about $2,100. Once you reach the cap, you pay nothing more for covered drugs that year.

What to do with those numbers:

1. Look up your plan's own deductible in the letter. Some plans charge less than the maximum, and some skip it for cheaper tiers.

2. If you take a brand-name drug, expect to meet the deductible in January or February. Set that money aside now.

3. If you've hit the cap in past years, budget $2,400 for drugs next year, plus premiums.

Only drugs your plan covers count toward the cap. A drug that isn't on your plan's list won't move you a single dollar closer to it.

14The tier each of your prescriptions sits on

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Every drug plan keeps a drug list, also called a formulary. Each drug on it sits on a tier, which is just its price level: low tiers for most generics, higher ones for pricier brand names.

Plans reshuffle every year. A drug can climb a tier, pick up new rules or drop off the list. The letter should flag changes, but check each drug yourself.

Call member services with your bottles in front of you and say:

"For 2027, is [drug name and strength] on your drug list? What tier is it, what's my copay, and does it need prior authorization or have a quantity limit?"

A quantity limit caps how much you can get at once. That matters if your doctor has you taking two pills where the plan expects one.

If a drug is coming off the list, ask your doctor whether a covered drug would work as well. If it wouldn't, your doctor can help you ask the plan for an exception before January.

13The free monthly payment plan for prescriptions

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That payment plan your drug plan keeps mentioning is worth a look, though not for everyone.

It's called the Medicare Prescription Payment Plan. Every Medicare drug plan offers it, and it's free. Instead of paying at the pharmacy counter, you get a monthly bill that spreads your drug costs across the year.

Be clear on what it doesn't do. It doesn't lower your total. It only changes when you pay.

It's worth it if a big deductible and a pricey brand name would land on you all at once in January. If you'd reach the $2,400 cap anyway, spreading it from January works out to about $200 a month instead of a huge bill in the first weeks of winter.

If your drugs are cheap generics, skip it. There's nothing to spread. You sign up through your drug plan or Advantage plan, and Medicare's payment plan page explains the details.

12Your separate drug plan's new monthly premium

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If you have Original Medicare (the government plan, often paired with a supplement) and a separate drug plan, look hard at that drug plan's premium line.

For 2027, there are no $0-premium standalone drug plans for people who don't get Extra Help. Some drug plan premiums are rising by more than $100 a month, more than $1,200 a year, for coverage that may be no better than before.

The math takes a minute. Subtract this year's monthly premium from next year's, then multiply by 12. That's what staying put costs before you fill a single prescription.

Extra Help is the federal program that helps people with limited income and savings pay for drug coverage. If money is tight, ask a counselor or Social Security whether you qualify. A yes would change every number on the page.

Your doctors, drugs and checkups

A plan can look fine on paper and still fail you at the front desk or the pharmacy window.

11The fifteen drugs with new Medicare prices

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On January 1, 2027, prices Medicare negotiated directly with drugmakers take effect for 15 drugs. Ozempic, Wegovy and Linzess are on the list.

If you take one of them, don't assume your copay falls on its own. What you pay still runs through your plan: the tier, the deductible, any prior authorization rule.

So check it like any other drug. Find it in next year's drug list, note the tier and the copay, and compare with what you pay now. If a plan you're considering puts it on a higher tier, you want to know that before December 7.

10Your doctors' names in next year's directory

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Skipping the provider directory is one of the most common mistakes people make this time of year. In an Advantage plan, the network decides almost everything. A doctor who's in-network this year can be out next year, and so can a hospital.

The directory is a start. The front desk is the answer. Next time you're at check-out, or calling about a refill, say:

"Will Dr. [name] be in-network with [exact plan name] in 2027?"

Use the exact plan name, not just the insurance company. One insurer can sell several plans with different networks.

Ask about your primary care doctor, each specialist, the hospital you'd want an ambulance to take you to, and wherever you get mammograms and lab work. Note the date and the name of whoever answered.

9The pharmacy where you actually pick up refills

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You've used the same pharmacy for years. The pharmacist knows your name and your birthday without asking. Your plan may not feel the same loyalty.

Drug plans have networks too. Many split pharmacies into preferred and standard, with lower copays at preferred ones. Your pharmacy can switch categories from one year to the next, or leave the network.

Quick test: look up your pharmacy in the plan's 2027 pharmacy directory, or ask at the counter whether it will be a preferred pharmacy for your plan next year.

If your plan offers mail order, price that too for drugs you take every day. A 90-day supply by mail can cost less than three trips to the counter.

See more: 25 Walkable Cities for Retirees →

8The women's screenings you're due for next year

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If you might switch plans, check what your regular screenings cost under the new one before you need them.

Under Original Medicare, a yearly screening mammogram costs you nothing if the provider accepts assignment, meaning they take Medicare's approved price. A follow-up, or diagnostic, mammogram is different: you pay 20% after the Part B deductible. Medicare's mammogram page lays it out.

That follow-up is where plans differ. In an Advantage plan, look up the copay for a diagnostic mammogram, since that's the bill that comes after a callback.

Before you switch, call the new plan and ask what a diagnostic mammogram would cost at the imaging center you already use.

7The plan's service area and your winter address

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Do you spend part of the winter somewhere warmer? Or are you thinking about moving closer to family?

Medicare Advantage plans are built around a service area, usually a set of counties. Outside it, a plan typically covers emergencies and urgent care and not much else. Plans can also shrink their service areas from year to year.

Check two things. First, that your county is still in your plan's area for 2027. Second, if you're away for weeks at a time, what the plan covers there. Some plans include travel benefits; many don't.

If you're moving, tell your plan and Social Security before you go. A move out of the area changes which plans you can choose.

With a supplement instead, call the insurer before a move and ask what changes. Most supplements work with any doctor in the country who takes Medicare, but the premium can depend on where you live.

See more: 23 Reasons Staying Put Costs More Than People Admit →

The dates that lock you in

Medicare runs on deadlines, and a few of them follow you for years.

6December 7 circled on your calendar

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Open enrollment for 2027 coverage is underway now and ends December 7. Anything you choose starts January 1.

If you do nothing and your plan is still offered, it renews automatically, changes and all. That's fine if you've checked and you're happy. It's a gamble if the letter never left the drawer.

Waiting until January is one of the classic mistakes. By then the new copays are live and the main window has closed.

Work backward from the deadline:

  • By mid-November: letter read, drugs and doctors checked.
  • By Thanksgiving: comparison done, counselor called if you want help.
  • First week of December: enroll, and write down the confirmation number.

That leaves room for a long hold on the phone or a second question. Help lines tend to get busier as December 7 gets close.

5Any stretch of time without drug coverage

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I don't take any prescriptions. Why pay for a drug plan?

Because of the late penalty. If you go 63 days or more in a row without Medicare drug coverage or other creditable coverage (coverage at least as good as Medicare's), you can owe a late enrollment penalty when you sign up later.

It's 1% of the national base premium for every month you went without. The base premium is about $39 in 2026, so a full year uncovered adds roughly $4.70 a month. The base can change each year.

That charge stays on your premium for as long as you have Medicare drug coverage, unless you qualify for Extra Help.

Still working, or covered through a spouse's job? Employer plans send a yearly notice saying whether their drug coverage is creditable. Keep it somewhere you can find it. If that job is ending soon, the 63-day clock starts the day the employer coverage stops.

4The January to March do-over for Advantage members

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If you're in a Medicare Advantage plan on January 1, you get one more chance to switch between January 1 and March 31. You can move to a different Advantage plan, or go back to Original Medicare and add a drug plan.

This is the fix if you realize in January that you joined an Advantage plan by mistake, or picked one without drug coverage.

It's one switch, not a rolling trial. It also isn't for everyone. If you have Original Medicare with a separate drug plan, this window doesn't apply to you.

There's a catch for anyone using it to leave Advantage. Going back to Original Medicare doesn't bring a supplement with it. Outside certain protections, a supplement insurer can ask about your health and say no.

3Your route back to a Medicare supplement

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If I leave Medicare Advantage, can I get a supplement back?

Maybe. It depends on timing and on your state. In most places, a supplement (also called Medigap) is guaranteed only during certain windows. Outside them, insurers can use underwriting, meaning health questions before approval, and they can charge more or turn you down.

Original Medicare on its own has no yearly cap on what you pay, which is why a supplement matters so much. Know your way back before you give one up.

If none of those fit you and you have health conditions, think hard before trading a supplement for an Advantage plan. Call a supplement insurer first and ask whether you'd face health questions to come back.

Getting it done, with help

You don't have to do the comparison alone, and you shouldn't have to pay anyone to help.

2A free session with a SHIP counselor

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Every state has a State Health Insurance Assistance Program, or SHIP. Its counselors give free one-on-one help with Medicare, and they don't sell plans. You can find yours at shiphelp.org.

Call and say: "I'd like help comparing my Medicare options for 2027. When can I get an appointment?"

Bring your Medicare card, your current plan card, the plan changes letter, and every drug you take with its strength and dose. Add the names of your doctors and your pharmacy.

Two more free lines worth saving in your phone:

  • Medicare Rights Center: 800-333-4114
  • 1-800-MEDICARE: 800-633-4227, open 24 hours a day

Agents and brokers can help too, but insurers pay them. If you use one, run their pick past a SHIP counselor before you enroll.

1Your pill bottles entered into Medicare's Plan Finder

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1. Gather every prescription you take: pills, inhalers, eye drops, insulin. For each, write down the name, the strength and how many you use in a month.

2. Go to Medicare's Plan Finder. You can browse without logging in. Logging in to your Medicare account saves your drug list for next time.

3. Enter your ZIP code, your drugs and the pharmacy you use.

4. Look at each plan's estimated yearly total for 2027, premium and drug costs together. Find your current plan, then compare it with the two or three lowest.

5. For any plan that comes out ahead, call your doctors' offices to confirm the network. Then enroll on the site or by calling 1-800-MEDICARE.

Why it's worth the trouble: it prices your actual drugs at your actual pharmacy across the whole year, premium included. That's the comparison the letter can't make for you, and most people never run it.

If your current plan comes out lowest, keep it, and know that you chose it.

The bottom line

The first thing to do is small. Take the plan changes letter out of the drawer tonight and read only the summary table near the front.

If nothing important moved, your drugs are on the same tiers and your doctors confirm they're staying in-network, let the plan renew. You're finished until next fall.

If something did move, run your drugs through Plan Finder before Thanksgiving and book a SHIP session. If you're in Advantage and tempted to leave, check your supplement options before December 7, not after.

Then put the letter back in the drawer with the date you're calling written on the envelope.

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Sources cited in this article

This article links to 10 outside sources, listed here so you can read them yourself.

  1. 55% of people on Medicare www.kff.org/medicare/10-key-facts-about-women-with-medicare
  2. Form SSA-44 www.ssa.gov/forms/ssa-44.pdf
  3. Medicare's payment plan page www.medicare.gov/prescription-payment-plan
  4. Medicare's mammogram page www.medicare.gov/coverage/mammograms
  5. Late enrollment penalty www.medicare.gov/drug-coverage-part-d/costs-for-medicare-drug-coverage/part-…
  6. Know your way back www.kff.org/medicare/medigap-may-be-elusive-for-medicare-beneficiaries-with-…
  7. Shiphelp.org www.shiphelp.org
  8. Medicare's Plan Finder www.medicare.gov/plan-compare
  9. Bone density test www.medicare.gov/coverage/bone-mass-measurements
  10. Pap test, pelvic exam and clinical breast exam www.medicare.gov/coverage/cervical-vaginal-cancer-screenings

Peter Byalik

Food & Home Editor

Peter Byalik is a professional chef with more than 20 years of experience, including years running his own business. He came to the United States from Ukraine.

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