The window
Medicare's Annual Enrollment Period runs October 15 through December 7 every year. Anything you change takes effect January 1, and the plan must have your request by December 7. There is no grace period after that date.
What you can do
Medicare is specific about what this window allows:
- Join a Medicare Advantage plan, with or without drug coverage
- Drop a Medicare Advantage plan and return to Original Medicare
- Switch from one Medicare Advantage plan to another
- Add drug coverage, or drop it
- Switch from Original Medicare to a Medicare Advantage plan
- Join, drop, or switch a Part D drug plan if you are on Original Medicare
In practice that covers almost every change most people want to make to how their Medicare works.
What this window does not do
This is where people get caught, and it matters.
Medicare Supplement plans are not part of Annual Enrollment. A Medigap policy is sold under different rules. You can apply at any time of year, but outside your one-time Medigap open enrollment window, insurers in most situations may ask health questions and may decline you or charge more based on your answers.
So if your plan is to leave Medicare Advantage during AEP and pick up a Supplement instead, understand the sequence: dropping the Advantage plan is easy, and being accepted for the Supplement may not be. Apply for the Supplement and get an approval before you drop anything.
The difference between the two paths is covered in Medicare Advantage versus Medicare Supplement.
The Part D numbers for 2027
If you are reviewing drug coverage, two figures changed for 2027.
| Part D | 2026 | 2027 |
|---|---|---|
| Maximum plan deductible | $615 | $700 |
| Out-of-pocket cap | $2,100 | $2,400 |
No Medicare drug plan may charge a deductible above $700 in 2027, and some plans have no deductible at all. Once your out-of-pocket spending on covered Part D drugs reaches $2,400, you move into catastrophic coverage and pay nothing for covered Part D drugs for the rest of the calendar year.
In between, during the initial coverage stage, you pay 25% coinsurance on generic and brand-name drugs.
Why the drug plan deserves the most attention
Part D plans change more than anything else in Medicare from one year to the next, and the changes are the least visible.
Formularies are rewritten annually. A drug can move to a higher tier, pick up a prior authorization requirement, or come off the list entirely. Pharmacy networks change too, and a plan that was cheapest at your pharmacy last year may not be this year.
The premium is the number people compare and the least important one. What matters is what your specific medications cost on that specific plan at the pharmacy you actually use.
What happens if you do nothing
You are not dropped. Your current plan generally continues into next year, with whatever changes the carrier made to it.
That is a safety net, not a decision. The plan continuing does not mean the plan is still right, and the changes carriers make are described in a notice they send each fall rather than in a phone call.
The second window most people do not know about
If you are already in a Medicare Advantage plan, there is another opportunity after AEP closes. The Medicare Advantage Open Enrollment Period runs January 1 through March 31, and during it you can switch to a different Advantage plan or drop back to Original Medicare.
It is only available to people already enrolled in an Advantage plan, and it is more limited than AEP. But it is a genuine second chance, and it is covered in AEP versus the Medicare Advantage Open Enrollment Period.
A note on the noise
From October onward the television advertising becomes relentless, and much of it is designed to make one plan sound universally best. No plan is.
The right plan depends on your medications, your doctors, the pharmacy you use, and how you prefer to handle costs. An advertisement cannot know any of those things.
How to review a drug plan properly
If you do one thing during Annual Enrollment, do this, because Part D is where the money moves.
Write down every medication with its exact dosage and how often you take it. Generic and brand names both, since plans treat them differently.
Note your pharmacy. Plans have preferred and standard pharmacy networks, and the same drug on the same plan can cost meaningfully more at a standard pharmacy than a preferred one.
Check each drug against next year's formulary, not this year's. Note the tier and whether prior authorization or step therapy applies.
Compare total annual cost, not monthly premium. Twelve months of premium, plus the deductible if the plan has one, plus what you will actually pay for your drugs across the year.
A plan with a $0 premium that puts one of your medications on a high tier can cost far more over twelve months than a plan with a $40 monthly premium that covers it well.
What the 2027 out-of-pocket cap means in practice
Once your out-of-pocket spending on covered Part D drugs reaches $2,400 in 2027, you pay nothing more for covered Part D drugs for the rest of that calendar year.
For someone on expensive specialty medication, that ceiling is the most important number in Medicare. It converts an unpredictable year into a known maximum, and it resets each January.
It also changes how you should compare plans. If you are confident you will reach the cap, the question becomes how quickly and cheaply you get there, rather than what the monthly premium is.
Changes that are not changes
Two things people expect to handle during AEP that do not belong to it.
Signing up for Medicare in the first place. That is your Initial Enrollment Period around your 65th birthday, a different window with different rules. See when can I enroll in Medicare.
Changing Part B. Your Part B enrollment and premium are handled through Social Security, not through a plan, and AEP does not touch them.
How The Jordan Insurance Agency helps
The Jordan Insurance Agency is an independent agency in Charlotte, North Carolina. We are not tied to one carrier, so we can run your actual medication list against the plans available in your county and show you what each would cost you at your pharmacy.
We will also tell you plainly when your current plan is still the best fit, because often it is. Our help costs you nothing, and your premium is the same whether you enroll with us or on your own.

