Commentary · Retirement Planning

The Plan That Renews Without You.

Written by the William Allan team · Published 2026-10-26

What to check before your Medicare coverage rolls into 2027

Every fall, Medicare offers a deadline that is easy to ignore, because ignoring it seems to cost nothing.

If you do nothing during Open Enrollment, your current coverage generally continues into the new year. That is convenient. It is also the problem. The plan that renews in January is not always the plan you chose. Premiums, deductibles, the drug list, the pharmacies, and the doctors in the network can all change.

Most people let it ride. KFF reports that most Medicare beneficiaries did not compare their coverage options during a recent open enrollment period. KFF, Medicare Open Enrollment: Key Questions and Answers

This year's window runs from October 15 through December 7, 2026. Changes made in that window take effect January 1, 2027.

What Open Enrollment Covers

During Open Enrollment you can join, drop, or switch a Medicare Advantage plan, with or without drug coverage. You can move from Original Medicare to Medicare Advantage, or back. If you are in Original Medicare, you can join, drop, or switch a standalone Part D drug plan. The plan must receive your request by December 7. Medicare.gov, Joining a Plan

There is a second, narrower window for people already in a Medicare Advantage plan. From January 1 through March 31, they can make one change: switch to a different Medicare Advantage plan, or leave for Original Medicare and join a separate drug plan. Medicare.gov, Understanding Enrollment Periods It is a useful fallback. It is not a reason to skip the review now.

What Is Changing for 2027

Your plan's own changes come first. Medicare Advantage and Part D plans send an Annual Notice of Change each fall describing changes to coverage, costs, and more that take effect in January. Medicare.gov, Plan Annual Notice of Change If yours went into a drawer in September, it is the place to start.

Some changes apply to everyone with Part D. For 2027, CMS raised both the standard Part D deductible and the annual cap on out-of-pocket costs for covered drugs. CMS, CY 2027 Rate Announcement, Attachment V

CMS is also ending the Part D Premium Stabilization Demonstration, a temporary program for standalone drug plans that began in 2025, at the end of 2026. CMS, July 28, 2026 Part D announcement Even so, CMS projects the average monthly premium for standalone Part D plans to rise only slightly. CMS, September 28, 2026 press release An average is not your plan. Individual plans can move by much more in either direction, which is exactly why the comparison matters.

Medicare's negotiated prices for more Part D drugs take effect on January 1, 2027. If you take one of them, ask your plan how the change affects what you pay. Medicare.gov, Your Medicare in 2027

The 2027 Part B premium and deductible had not been announced when this was written. CMS usually publishes them in the fall.

The Decision That Is Hard to Undo

One choice deserves more care than the rest: leaving Original Medicare and a Medicare Supplement (Medigap) policy for a Medicare Advantage plan.

Open Enrollment lets you move between Original Medicare and Medicare Advantage. It does not give you a right to buy a Medigap policy. Outside your initial Medigap enrollment period, federal law generally does not require an insurer to sell you one except in specific situations, and a policy you can buy may cost more because of past or present health problems. Medicare.gov, When Can I Buy Medigap? Medicare's own guidance is blunt: if you drop your Medigap policy, in most cases you will not be able to get it back. Medicare.gov, Switching or Dropping Medigap

That means someone who drops a Medigap policy for a Medicare Advantage plan may not be able to get comparable Medigap coverage back years later, when their health may be different. Federal law includes a limited trial right. Someone who drops a Medigap policy to join Medicare Advantage for the first time, and leaves within the first year, can generally get that same policy back if the insurer still sells it. Medicare.gov, Choosing a Medigap Policy After the first year, getting Medigap back can depend on health and state law.

State rules can add protections. California gives people who already have a Medigap policy a window following their birthday each year to buy another policy with the same or fewer benefits, without medical screening. California Department of Insurance, Medicare Supplement Insurance Other states have different rules, and your state insurance department can tell you which apply.

None of this makes one choice right. Medicare Advantage plans can cost less up front and often bundle extra benefits. Original Medicare with Medigap generally offers broader access to providers who accept Medicare and more predictable costs. The point is to make the switch knowing whether you can switch back.

What to Bring to the Review

The review goes faster with these in hand:

• A current list of your prescriptions, with doses and how often you fill them, plus the pharmacy you use.
• The doctors, specialists, and hospitals you want to keep, if you are in or considering a Medicare Advantage plan.
• Your plan's Annual Notice of Change for 2027.
• Where you will be during the year. A plan with a local network may work poorly for someone who spends winters in another state.

Then enter your drugs in Medicare Plan Finder and compare estimated total yearly cost, not just the premium. A plan with no premium can cost more over a year than one with a premium if your drugs sit on a higher tier.

If your drug costs come in large amounts early in the year, the Medicare Prescription Payment Plan lets you spread out-of-pocket drug costs into monthly payments through your plan. It is free and voluntary. It does not lower what you pay; it changes when you pay it.

Where to Get Help Without a Sales Pitch

Fall brings a lot of Medicare mail and advertising. Medicare's own guidance is that Medicare.gov, the Medicare & You handbook, and 1-800-MEDICARE (1-800-633-4227) are the official sources.

Every state also has a State Health Insurance Assistance Program (SHIP) that offers free, unbiased, individualized counseling. In California it is called HICAP (1-800-434-0222). In Colorado, Colorado SHIP is at 888-696-7213. Other states are listed at shiphelp.org. Counselors get busier as December 7 approaches, so call early.

Where an Advisor Fits

Medicare is one of the larger and less predictable lines in a retirement budget, and it connects to the rest of the plan. Income can raise premiums through the surcharge we covered in our piece on Medicare IRMAA and the two-year lookback. And Medicare does not pay for long-term care, a gap we covered in the care plan most families skip.

William Allan is fee-only and is paid directly by clients. The firm does not earn commissions for selling investments, insurance, or proprietary products. We can help you fit health care costs into your retirement income plan; see our retirement planning approach.

Schedule a free introductory call with Ian, who handles first conversations for William Allan. The call is not advice; its purpose is to understand your situation and help arrange the right next step with the advisory team.

This commentary is for informational purposes only and is not investment, tax, insurance, or legal advice, and it is not a recommendation of any Medicare plan or type of coverage. All investing involves risk, including the possible loss of principal, and past performance does not guarantee future results. Medicare figures and enrollment rules were checked October 26, 2026, against Medicare.gov and CMS publications and can change; 2027 Part B amounts had not been published at that time. Plan costs, benefits, and networks vary by plan and location. Medigap rights vary by state; contact your state insurance department or SHIP for the rules that apply to you. William Allan does not provide tax or legal advice; tax preparation and tax advice, when provided, are through affiliated Crawshaw CPAs under a separate engagement. William Allan is an investment adviser registered with the SEC; registration does not imply any specific level of skill or training.