Medicare Open Enrollment Is Coming — Here’s What You Need to Do

If you’re on Medicare, you know what time of year is approaching.

Your mailbox is about to fill with Medicare Advantage brochures. Your television will feature an astonishing number of celebrities suggesting that you may be missing benefits you “deserve.” Text messages, emails, radio ads (if you’re still listening to radio). And somewhere along the way, someone will probably tell you that it’s time to reconsider your Medicare Supplement plan. 

Welcome to Medicare’s Annual Enrollment Period (AEP).

Or, as Medicare now more commonly calls it, Open Enrollment.

It runs every year from October 15 through December 7. Changes made during this period generally take effect January 1 of the following year.

For 2026, that means you’ll be reviewing coverage for 2027.

But before we get into what you should do during Open Enrollment, let’s clear up one of the biggest misconceptions about it.

Short version:

• Review Medicare Advantage and Part D coverage during Open Enrollment.
• Do not confuse it with Medigap Open Enrollment.
• Expect a higher maximum Part D deductible and out-of-pocket threshold in 2027.
• Compare 2027 costs and drug coverage even if you plan to keep your current coverage.

First: This Is NOT Medigap Open Enrollment

This creates a LOT of confusion. It doesn’t help that, as UnitedHealthcare puts it, “This is the only time each year anyone with Medicare coverage can make changes…” AEP/Open Enrollment isn’t for changing all Medicare choices.

During Medicare Open Enrollment, you can:

• Switch from one Medicare Advantage plan to another.
• Switch from Original Medicare to Medicare Advantage.
• Leave Medicare Advantage and return to Original Medicare.
• Join, drop, or change a standalone Medicare Part D prescription drug plan.

What you do not receive is a special annual opportunity to freely change your Medicare Supplement — commonly called Medigap — policy. 

That’s an entirely different thing.

Your primary federal Medigap Open Enrollment Period generally lasts for six months beginning when you’re at least 65 and enrolled in Medicare Part B.

Once that period is over, it does not magically reappear every October.

Depending on where you live and your circumstances, you may still be able to change Medigap plans. But unless you qualify for a guaranteed-issue right or have additional protections under your state’s law, an insurer may be able to ask health questions, medically underwrite you, charge you more, or decline your application.

So:

Medicare Open Enrollment ≠ Medigap Open Enrollment.

That becomes especially important if you are considering leaving Medicare Advantage and returning to Original Medicare.

Leaving Medicare Advantage? Check Medigap BEFORE You Switch

Medicare Open Enrollment allows you to leave Medicare Advantage and return to Original Medicare.

It does not, by itself, guarantee that you can buy the Medigap policy you want afterward.

There are exceptions.

For example, Medicare provides certain “trial rights” if you joined Medicare Advantage when you first became eligible for Medicare at 65 and decide within the first year that you want to return to Original Medicare.

There are also protections in certain situations, such as when plans terminate coverage, you move outside a plan’s service area, or other qualifying events occur. State laws can provide additional protections.

But there is no blanket rule saying:

I switched from Medicare Advantage back to Original Medicare during AEP, therefore every Medigap company has to accept me.

That can be a very expensive assumption.

If you’re considering switching from Medicare Advantage to Original Medicare and expect to buy Medigap coverage, check your Medigap eligibility before you switch.

This is one Medicare decision where clicking first and asking questions later is a particularly bad strategy.

Part D Is Changing Again in 2027

For people using standalone Medicare Part D prescription drug coverage — or drug coverage included in a Medicare Advantage plan — two important numbers are increasing for 2027.

Part D cost	2026	2027
Maximum deductible	$615	$700
Out-of-pocket threshold	$2,100	$2,400

One important clarification: $700 is the maximum deductible Medicare allows, not necessarily the deductible your particular plan will charge. Some plans have lower deductibles, and some have no deductible. None can charge more than $700 in 2027.

Likewise, the $2,400 out-of-pocket limit does not mean that once you’ve paid $2,400 in premiums and prescription costs, Medicare takes over.

Your monthly Part D premiums do not count toward that $2,400 threshold. You may hear this called a Part D “MOOP,” but I avoid that term here. MOOP is more commonly used for the annual limit on covered medical spending in Medicare Advantage — and premiums don’t count toward that limit, either.

The Part D threshold applies to qualifying spending on drugs covered by your plan, including certain payments made on your behalf. Once you reach it, you enter catastrophic coverage and pay no additional cost sharing for covered Part D medications for the remainder of the year. “Covered” is a key word here. If your plan doesn’t cover a drug, what you pay for it generally won’t count toward the out-of-pocket threshold — unless the plan approves a formulary exception.

The Centers for Medicare & Medicaid Services (CMS), the federal agency that administers Medicare, adjusts these benefit parameters annually.

Do I Really Need to Shop My Part D Plan Every Year?

Need to?

No.

Should you?

Absolutely.

There is no requirement that you change plans every year. If your existing plan still works best for you, doing absolutely nothing may be the smartest choice.

But you shouldn’t assume that because your Part D plan worked well in 2026, it will remain your best choice in 2027.

Prescription drug plans can change:

• Premiums
• Deductibles
• Copays and coinsurance
• Formularies — the list of drugs the plan covers
• Drug tiers
• Prior-authorization requirements
• Quantity limits
• Preferred pharmacy arrangements
• Mail-order pricing

And of course, you may have changed.

Maybe your doctor added a medication. Maybe you stopped taking another. Maybe a generic became available. Maybe you changed pharmacies.

Your plan should send you an Annual Notice of Change, or ANOC, each fall detailing changes that take effect January 1.

Read it.

Yes, I realize I just recommended reading an insurance document.

Retirement is full of unexpected developments.

Good to know: When should your ANOC arrive? Plans must send it by September 30. “Send” and “arrive” are not necessarily the same thing, of course. If yours hasn’t appeared, check your insurance company’s website or online account; it may be available there before the paper version reaches your mailbox.

Loyalty Is a Terrible Part D Strategy

There is very little reason to be loyal to a prescription drug plan.

Your insurance company does not send you a Christmas ham because you’ve been with them for eight years.

What matters is whether the plan covers your particular medications, at pharmacies convenient to you, at the lowest reasonable overall cost.

Two neighbors living in identical houses may have completely different “best” Part D plans because they take different medications.

Even two people taking exactly the same medications could get different results if one fills prescriptions at CVS and the other uses H-E-B, Walmart, Walgreens, Costco, or a mail-order pharmacy.

This is why comparing plans based solely on the monthly premium is a mistake.

A $5 monthly premium looks wonderful, right up until one prescription costs you an extra $80 every month.

What you care about is total estimated annual cost.

Fortunately, Medicare provides a pretty good tool for figuring that out.

First, Create a Medicare.gov Account

If you don’t already have a Medicare.gov account, I’d recommend creating one before Open Enrollment begins.

I’ve always been mystified by how many people don’t have a Medicare.gov account. After all, it’s free, secure, and incredibly useful. 

Among other things, your account allows you to:

• See your current Medicare coverage.
• Save your medications.
• Save your pharmacies.
• Compare health and prescription drug plans using that information.
• View Original Medicare claims.
• Print a Medicare card.
• Access Medicare documents electronically.

Having an account does not change your coverage, enroll you in anything, or obligate you to receive Medicare information electronically.

And for Part D shopping, being able to save your medications and pharmacies makes the process so much easier.

If you’re comfortable enough using the internet to be reading Retired.Living, you really should have a Medicare.gov account.

There. I’ve said it.

How to Compare Part D Plans on Medicare.gov

Once Medicare releases the 2027 plans available in your area, go to Medicare.gov and use its Plan Compare tool.

You can browse without an account, but logging in makes things easier because Medicare can save your information.

1. Enter every medication you take.

Be specific.

Enter:

• The exact drug
• Dosage
• Quantity
• How often you refill it

“Lisinopril” isn’t enough if Medicare is trying to estimate what you’ll actually spend.

This is a good time to grab your prescription bottles rather than relying on memory.

2. Enter several pharmacies.

Don’t assume your favorite pharmacy will have the best prices under every plan.

Part D plans can designate certain pharmacies as preferred pharmacies, where members may pay lower copays or coinsurance than they would at another pharmacy that’s still technically “in network.”

Try two or three pharmacies you would realistically use.

You may be surprised by the difference.

3. Look at estimated TOTAL yearly cost.

This is the big one.

Do not sort plans based solely on the monthly premium.

Medicare’s Plan Compare tool can estimate your total annual costs based on the medications you’ve entered.

That gives you a much more useful comparison:

Premiums + estimated prescription costs

A plan charging $25 a month might ultimately cost you less than a $0-premium plan.

Math remains stubbornly annoying that way.

4. Make sure every medication is covered.

Check the plan formulary.

Also look for:

• Prior authorization
• Step therapy
• Quantity limits
• Drug tier
• Deductible treatment

A low estimated price isn’t nearly as exciting if your most important medication isn’t covered.

5. Enroll if you find something better.

If another plan makes more sense, you can enroll directly through Medicare.gov.

When you enroll in a new Part D plan during Open Enrollment, you generally do not need to separately cancel your existing Part D plan. Your old coverage ends when the new plan begins.

And if your existing plan remains your best option?

Do nothing.

Congratulations. You have successfully completed Medicare Open Enrollment without actually changing anything.

That’s a perfectly legitimate outcome.

Wait. Didn’t My Medicare Broker Used to Do This for Me?

Quite possibly.

And this is another change that’s frustrating some Medicare beneficiaries.

A growing number of insurance brokers either no longer review standalone Part D plans for clients or offer much less assistance with them.

Medicare hasn’t prohibited brokers from helping you.

The problem is economics.

Agents and brokers have to maintain licenses, complete Medicare certifications, follow extensive marketing and compliance requirements, collect medication information, compare formularies and pharmacies, explain plan differences, and sometimes help complete enrollment.

Meanwhile, some Part D plans pay very small commissions — and some pay brokers nothing at all.

In 2024, for example, Wellcare announced that it would stop paying agents commissions on its standalone Part D plans beginning with the 2025 plan year.

The Medicare Payment Advisory Commission, or MedPAC, has since examined the broader issue of zero-dollar commissions and the effect they can have on beneficiaries’ access to agents.

Think about the business problem.

A broker may spend substantial time comparing your medications among several plans, discover that the plan that’s clearly best for you pays no commission, enroll you in it — and earn precisely zero dollars for the work.

You can hardly blame some brokers for deciding that’s not a sustainable business model.

This doesn’t mean every broker has stopped helping with Part D. Many still do.

Just don’t be surprised if yours doesn’t.

What If I Want Help From an Actual Human?

There is another option, and it’s a good one.

Every state has a State Health Insurance Assistance Program, usually called SHIP.

SHIP provides free, personalized Medicare counseling and is not affiliated with an insurance company or health plan.

Counselors can help Medicare beneficiaries understand coverage, compare plans, evaluate costs, and navigate enrollment decisions.

You can also call 1-800-MEDICARE for assistance.

So if Plan Compare leaves you staring at your computer like it’s displaying hieroglyphics, you aren’t stuck figuring everything out alone.

What About the Medicare Prescription Payment Plan?

One more Part D feature is worth knowing about, particularly if you take expensive medications.

The Medicare Prescription Payment Plan allows people with Medicare drug coverage to spread their out-of-pocket prescription costs across the calendar year instead of potentially paying a large amount at the pharmacy early in the year.

This can help with cash flow.

But here’s the important part:

It does not reduce the cost of your medications.

It only changes when you pay the bill.

If you have significant prescription expenses early in the year, spreading those costs over several months may make budgeting easier.

Just don’t mistake spreading your drug costs for reducing them.

One More Part D Change Worth Watching

There is another behind-the-scenes change occurring in 2027.

CMS is ending something called the Part D Premium Stabilization Demonstration at the end of 2026.

The program was introduced when major changes to the Part D benefit took effect and was designed to help reduce volatility in premiums for standalone prescription drug plans.

CMS says insurers now have enough experience operating under the redesigned Part D system to return to regular market conditions.

The administration reportedly estimates that approximately 75% of people enrolled in standalone Part D plans will see higher premiums in 2027. That does not mean everyone’s premium will increase — or that everyone with Part D is affected. Actual premiums will vary by plan and location, providing yet another reason to check your specific coverage.

You do not need to understand the actuarial plumbing behind this.

I certainly don’t plan to spend my retirement modeling insurance-company bids.

But it reinforces the larger point:

Don’t assume your 2027 premium or plan design will look like 2026.

Check.

Your Medicare Open Enrollment To-Do List

Despite thousands of pages of Medicare regulations, your actual Open Enrollment assignment isn’t particularly complicated.

Before October 15:

• Create or make sure you can access your Medicare.gov account.
• Make an accurate list of your current prescriptions.
• Gather your Annual Notice of Change from your existing plan.
• Think about which pharmacies you’re willing to use.

Once 2027 plans become available for comparison:

• Enter your medications into Medicare Plan Compare.
• Compare several realistic pharmacies.
• Look at total estimated annual cost, not just premium.
• Check formulary coverage and restrictions.
• Compare the results with your current plan.

Then make a decision.

Maybe you’ll switch.

Maybe you’ll save several hundred dollars.

Maybe you’ll discover your existing plan is still the best choice and change absolutely nothing.

All three are perfectly reasonable outcomes.

The mistake isn’t staying with your current Medicare plan.

The mistake is staying with it without checking.

Twenty or thirty minutes on Medicare.gov once a year seems like a pretty reasonable investment to make sure an insurance company hasn’t quietly moved the financial furniture around while you weren’t looking.

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More Information

Here is a useful video featuring Danielle Kunkle Roberts, co-founder of Boomer Benefits. It discusses Part D and covers many of the points made in this article: