What to Review During Medicare Open Enrollment for 2027

By Madison Bennett, CFP®, CFT-I™

The Medicare mail starts arriving in September, and most of it looks just like last September’s, which can make it tempting to skim and move on. However, integrating this review into your broader financial planning is essential, because treating open enrollment as a passive event is how people end up stuck in mismatched coverage. Doing nothing is an active choice, and insurance providers revise their pricing and drug lists every single year. 

Below is what the enrollment period lets you change and what to compare before you decide.

When Open Enrollment Happens and What You Can Change

Medicare’s fall open enrollment runs from October 15 through December 7 every year, with changes taking effect January 1. For 2027 coverage, the window is October 15 to December 7, 2026.

What you can do depends on the coverage you hold now:

• With Parts A and B, you can move to a Medicare Advantage plan (Part C).
• With a Medicare Advantage plan, you can return to Original Medicare or choose a different Advantage plan.
• With a Part D drug plan, you can switch plans or drop the coverage.
• If you’ve never had Part C or Part D, you can enroll for the first time.

Do nothing and your coverage carries into the new year. Open enrollment is also not how you join Medicare. Initial enrollment is tied to your birthday, spanning three months either side of the month you turn 65.

What to Compare Before December 7

Your plan must mail you an Annual Notice of Change by September 30. It lists every revision coming in January. Four items to pay attention to:

• Your prescriptions: Confirm each medication you take is still on the plan’s covered drug list and check its tier. A drug moving up a tier can change your cost more than a premium increase does.
• Your pharmacy: Plans designate preferred pharmacies and revise those arrangements annually, so the same prescription can cost two different amounts within one plan.
• Your physicians: For Medicare Advantage, verify your doctors and hospitals are in network for 2027.
• Total annual cost: A low premium paired with a high deductible can cost more over 12 months than the reverse.

One further point if you’re considering a move from Medicare Advantage to Original Medicare: returning is straightforward, but adding a Medigap policy alongside it may not be. 

Outside certain protected windows, most states permit Medigap insurers to review your medical history and either charge more or decline the application. One such window covers the first 12 months of your first Advantage plan. 

Sort out the Medigap question before dropping the Advantage plan.

If You Worked Past 65 and Are Retiring Soon

The rules shift once your coverage comes from current employment. 

A group health plan through your own or your spouse’s active job qualifies you for a special enrollment period when that employment or coverage ends, whichever comes first. 

From that point you have eight months to enroll in Part B without a permanent late penalty, and Social Security will not take your word for it. Two documents do that work.

• Form CMS-L564, Request for Employment Information: Your employer completes a section verifying the dates you were covered by the group plan based on current employment, and you submit it with Form CMS-40B, the Part B application. Without it, Social Security has no record of qualifying coverage after 65, and a late penalty attaches to your Part B premium permanently.
• A creditable coverage letter: Your employer plan should send a notice each year stating whether its drug coverage meets Medicare’s minimum standard. Keep it, because that letter is your evidence when you enroll in Part D. A gap of 63 days or more without creditable drug coverage triggers a separate lifetime penalty.

Request both from HR before your last day, since chasing a signature from a former employer becomes a low priority once you’re gone. 

One thing catches people off guard: COBRA does not extend the eight-month window, which starts when active employment coverage ends.

What’s Changing for 2027 Coverage

Two Part D figures are already set. The annual cap on out-of-pocket costs for covered prescriptions rises to $2,400 from $2,100, and the standard deductible increases to $700 from $615. 

Vaccines recommended by the CDC’s advisory committee and covered insulin products remain exempt from the deductible, with insulin cost sharing capped at $35 per month.

Premiums are less settled. The standard Part B premium is $202.90 per month in 2026, and CMS typically announces the next year’s figure in November. 

The most recent Medicare Trustees projection places the 2027 premium near $209.50, though the final figure may differ. Part D premiums are set by private insurers and vary widely, some with none at all.

Where Medicare Meets Your Tax Return

Medicare premiums also run on a two-year delay, which is what surprises higher-income households navigating 2027 coverage.

A Roth conversion or a business sale in 2025 can raise your Part B and Part D premiums two years later in 2027 through the income-related monthly adjustment amount, known as IRMAA.

For 2027 coverage (which looks back at your 2025 tax return), those surcharges are projected to begin at $111,000 of modified adjusted gross income for a single filer and $222,000 for a couple filing jointly, with crossing a threshold by a single dollar still pushing you into the full higher tier.

That lookback is why enrollment decisions and tax planning belong in the same conversation. If you’re retiring within the next year, this is a good time to pressure-test the sequence. A second set of eyes can surface items you did not know to ask about, including forms like the L564. 

That’s the type of question we walk through during a Financial Physical®, a structured review of where your planning stands.

To reach our team, call (410) 823-7283, or schedule a time through our website.

Frequently Asked Questions About Medicare Open Enrollment

When is Medicare open enrollment for 2027 coverage?

Medicare open enrollment for 2027 coverage runs from October 15 through December 7, 2026. Plan changes take effect January 1, 2027. Your current plan must mail its Annual Notice of Change by September 30, 2026, which gives you about two weeks to review next year’s costs and drug coverage before the window opens.

What happens if I do nothing during Medicare open enrollment?

Your current plan renews automatically into the following year, along with any changes the plan has made to its premium, deductible, covered drug list, or provider network. Automatic renewal is the most common outcome, and it is also why the Annual Notice of Change deserves 15 minutes of your time each fall.

How much will Medicare Part D cost in 2027?

For 2027, the standard Part D deductible is $700 and the annual out-of-pocket cap on covered prescriptions is $2,400. After you reach that cap, covered medications cost you nothing for the rest of the year. Premiums and deductibles vary by plan, since private insurers set their own pricing.

Do I have to sign up for Medicare during open enrollment if I am still working at 65?

No. Group health coverage through current employment qualifies you for a special enrollment period instead of the fall window. That period gives you eight months after employment or coverage ends to enroll in Part B without a penalty. Financial Consulate walks pre-retirees through this timing before a retirement date becomes final.

What is Form CMS-L564 and why do I need it?

Form CMS-L564, Request for Employment Information, is the document your employer completes to verify you had group health coverage based on current employment after age 65. You submit it with Form CMS-40B, your Part B application. Without it, Social Security cannot confirm you qualify for a penalty-free special enrollment period.

About Madison

Madison Bennet, CFP®, CFT-I™, is a Wealth Advisor at Financial Consulate, where she works directly with clients to help them stay aligned with their long-term financial goals. Her planning work includes tax planning, estate planning, investment planning, and retirement planning.