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Retirement Money Brief

You have 63 days

By Ellen Marsh · September 22, 2026
RetireShield — Retirement Money Brief.

One October letter decides your 2027 coverage

WHAT CHANGED?

Insurance companies have already settled which Medicare plans they will keep selling next year, and a share of those plans will not be coming back. If yours is one of them, the company has to tell you in writing, and that letter is due in your mailbox by October 2.

Amazon Prime settlement: eligible customers can receive up to within 60 days.

Federal rules require at least 90 days' notice before a plan ends, which is why these envelopes always land in the same stretch of early autumn. What the letter rarely says plainly is the good part. A plan leaving is not a coverage emergency. It hands you two protections almost nobody else gets, and both of them run on a clock.

WHO IS AFFECTED?

  • Anyone whose Medicare Advantage plan or standalone drug plan is ending for 2027, or is pulling out of the county where you live.

  • Anyone who has ever been turned down for a Medicare Supplement policy, or assumed a health condition ruled one out. A plan leaving reopens that door.

  • Not you, if the letter only lists new costs or benefits for next year. That is the Annual Notice of Change, a separate letter due by September 30.

WHAT DOES IT MEAN?

Start with the calendar, because every date on it works in your favor.

Everyone gets Medicare Open Enrollment, October 15 through December 7. If your plan is not renewing, you also get a private extension on top of it: you may switch from December 8 through the last day of February.

Do nothing at all and you are still not stranded. You land in Original Medicare on January 1. But Original Medicare on its own sets no yearly limit on what you pay out of pocket. None. This year the hospital deductible runs $1,736 for each benefit period, the 2027 figures are not published yet, and the 20 percent share you owe on doctor visits and outpatient care simply keeps going. Closing that gap is exactly what a Medicare Supplement policy, also called Medigap, is built to do.

Which brings me to the protection I most want you to use. In an ordinary year a Medigap company may study your health history, charge you more for it, or turn you down outright. When your plan leaves, that stops. You get what is called a guaranteed issue right, and any Medigap policy sold in your state has to sell to you at its regular price. You may apply as early as 60 days before your coverage ends and no later than 63 days after it ends. Let that window shut and, in most states, your medical history goes back on the table.

One trap to step around on the way: Original Medicare does not include drug coverage. Go 63 days or longer without it and Medicare adds a penalty of 1 percent of the national base premium for every month you waited, and it stays on your bill for as long as you have drug coverage.

WHAT TO DO

Open every piece of mail your plan sends this month, including the envelopes that look like advertising, and read the top of each one for the words will not be renewed or will not be offered in 2027. If those words are there, put two dates on the calendar the same day: December 7, and the 63rd day after your coverage ends. Then use the weeks in between instead of the last one. Medicare's own guide to the plan mail arriving this month tells you which letter is which.


SOURCE: Medicare's rules for switching when a plan leaves

Written by Ellen Marsh

Retirement Money Brief is educational information only — not financial, tax, or legal advice. We will never ask you for an account number, Social Security number, password, or payment.

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