Medicare Annual Enrollment Period
Updated October 2026
Each fall, Medicare's Annual Enrollment Period (October 15 through December 7, often called "open enrollment") lets you review your coverage and make changes for the coming year. Changes take effect January 1.
Many people let their coverage renew automatically. That's understandable, but plans change every year, and so do our health needs. Spending an hour or two reviewing your options can save real money and help you avoid surprises.
What's new for 2027
Part D out-of-pocket cap: $2,400 (up from $2,100 in 2026). Once your out-of-pocket spending on covered drugs reaches the cap, you pay nothing more for covered drugs that year.
Part D deductible: up to $700 (from $615). Some plans set it lower.
Medicare GLP-1 Bridge: Part D generally doesn't cover GLP-1 drugs such as Wegovy and Zepbound when prescribed for weight loss. From July 1, 2026 through December 31, 2027, the temporary Medicare GLP-1 Bridge offers eligible Part D enrollees Wegovy, Zepbound (KwikPen), or Foundayo for $50 per month. Eligibility depends on BMI and certain health conditions, and your doctor submits a prior authorization to Medicare. The $50 copay does not count toward your Part D deductible or out-of-pocket cap, and Extra Help does not apply. If you already take a GLP-1 for a covered reason, such as Type 2 diabetes, you'll continue to get it through your regular Part D plan.
Fewer broker reviews: many insurers have stopped paying brokers commissions on Part D plans, so fewer brokers offer annual drug plan reviews.
Figures as published by CMS for 2027 and subject to change.
Why review it every year?
Medicare Advantage and Part D plans are not static. Each year:
Formularies change. Drugs may move to a different tier or be dropped entirely.
Premiums, deductibles, and copays adjust. What was a good value last year may not be now.
Networks change. Doctors, hospitals, and preferred pharmacies can leave a plan's network.
Plans come and go. Insurers have been adding, dropping, and restructuring plans in recent years. Your plan may look quite different next year, or may not be offered at all.
Your own needs change. New diagnoses, new prescriptions, or a move can change which plan fits best.
Your plan's Annual Notice of Change (ANOC), typically mailed by September 30, summarizes what's changing for next year. It's worth reading carefully, even if you plan to stay put.
When you can switch, and what to watch for
The rules differ quite a bit depending on your coverage type.
Medicare Advantage (Part C)
During the Annual Enrollment Period, you can switch to a different Medicare Advantage plan or return to Original Medicare. There's also a separate Medicare Advantage Open Enrollment Period from January 1 to March 31, during which you can make one change: switch to another Medicare Advantage plan, or drop Medicare Advantage and return to Original Medicare (adding a stand-alone Part D plan).
Before you switch, confirm your doctors are still in-network, and your medications are covered. And keep in mind that returning to Original Medicare doesn't guarantee you can buy a supplemental policy without medical underwriting.
Medigap (Medicare Supplement)
Medigap, commonly known as a supplement, works differently. It isn't tied to the fall enrollment window. You can apply for a new policy at any time, but outside of your initial enrollment period or a situation that grants guaranteed issue rights, insurers generally require medical underwriting. That means they can review your health history, charge you more, or deny coverage. In practical terms, this makes changing your Supplement a non-starter.
Medigap plans are standardized, so the coverages of a given plan letter don't change from year to year, but the premiums can. If your premium has risen, you can shop for another supplement (usually with underwriting) or consider Medicare Advantage (no underwriting). Just remember that you may not be able to get back into a Medigap plan later.
A few states have their own rules that allow some Medigap switches between carriers offering the same supplement without underwriting, so it's worth checking your state's rules. Virginia allows the so-called “birthday rule,” where Medigap carriers cannot deny coverage, charge higher premiums based on health status, or impose waiting periods for a special window around your birthday. Keep in mind that you can only switch between like supplements (e.g., Aetna Plan G to United Health Plan G).
Part D (Prescription Drug Plans)
If you have original Medicare with a supplement, you can change stand-alone Part D plans every year during the Annual Enrollment Period, with no medical underwriting. That flexibility is valuable, but only if you use it. More on this below under How to Compare Drug Coverage.
If you're moving
Medicare Advantage and Part D plans are regional, so a move may mean your current plan isn't available in your new area. Moving out of your Medicare Advantage plan's service area generally gives you a special enrollment period and, in many cases, guaranteed issue rights to return to Original Medicare with a Medigap policy. Medigap policies are portable, so moving generally doesn't create an opportunity to switch plans, but premiums will vary by location, so it's worth comparing prices in your new area.
How to compare drug coverage
Whether your drug coverage comes from a stand-alone Part D plan or a Medicare Advantage plan, the same approach applies.
1. Start with your medication list
Gather each drug, dose, and how often you take it. This is the single most important input.
2. Understand how the out-of-pocket cap changes the math
Since 2025, Medicare has eliminated the old coverage gap (the "doughnut hole") and added an annual out-of-pocket cap on Part D drug costs. The cap is the same on every plan, including the lowest-premium options. That has changed how plans compare:
If you take expensive brand-name or specialty drugs, you may reach the cap under any plan that covers them. In that case, a lower-premium plan may cost you less overall, since your out-of-pocket ceiling is the same either way. What matters most is that the plan covers each of your drugs without burdensome restrictions like prior authorization or step therapy.
If you take mostly generics, you're unlikely to reach the cap, so differences in premiums, deductibles, and copays still matter. A low-premium plan often makes sense.
One important caveat: the cap only counts drugs that are on your plan's formulary (or approved through an exception) and filled at a network pharmacy. A drug your plan doesn't cover doesn't count toward the cap.
If you expect to reach the cap, the Medicare Prescription Payment Plan lets you spread your out-of-pocket costs into monthly payments rather than paying most of it early in the year. It doesn't reduce what you owe, but it can help with cash flow.
3. Look at total annual cost, not just premium
The goal is to minimize your total yearly expense: premiums plus deductibles, copays, and coinsurance. A few other things can make a difference:
Preferred pharmacies. Many plans offer lower copays at preferred pharmacies. Switching where you fill prescriptions can sometimes save as much as switching plans.
Extra Help. If you have limited income and assets, the federal Extra Help program can significantly reduce premiums and out-of-pocket costs. Eligibility was expanded in 2024, so it may be worth checking even if you didn't qualify before.
4. Know when paying cash makes sense
Several tools let you buy medications outside of insurance:
GoodRx: digital coupons accepted at most retail pharmacies.
Mark Cuban Cost Plus Drug Company: mail-order generics priced at cost plus a small, published markup.
TrumpRx: a federal price-comparison and coupon site for certain brand-name drugs.
These can sometimes beat your plan's price, especially for inexpensive generics or drugs your plan doesn't cover. But when you use them, you're a cash-pay customer, and none of that spending counts toward your Part D deductible or out-of-pocket cap. For people on expensive medications, filling through your plan is generally the safer choice.
Where to get help
Medicare Plan Finder. The official tool at Medicare.gov lets you enter your ZIP code, pharmacies, and medications, then compare stand-alone Part D plans and Medicare Advantage plans side by side, including estimated annual costs and star ratings.
Step-by-step guidance. The Steinlage Insurance Agency's Medicare Part D Resource Center walks through the Plan Finder and other aspects of shopping for drug coverage.
Free counseling. Your state's SHIP (State Health Insurance Assistance Program) offers free, unbiased Medicare counseling. In Virginia, it's called VICAP. You can also call 1-800-MEDICARE.
Paid consultants. Independent Medicare consultants offer plan reviews for a fee.
The Bottom Line
Open enrollment is your once-a-year chance to make sure your coverage still fits. Read your Annual Notice of Change, run your current medication list through the Plan Finder, and think about whether your health needs or location have changed.
Oakleigh clients are welcome to reach out for help thinking through their options. When a situation calls for more specialized help, we can refer you to an outside Medicare expert.
