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#Medicare Supplement

When Can I Sign Up for a Medicare Supplement Plan in Colorado?

Uncle Sheldon

By Uncle Sheldon

Uncle Sheldon Writing Team

Published Oct 6, 2026 3 min read
When Can I Sign Up for a Medicare Supplement Plan in Colorado?

You can apply for a Medicare Supplement plan, also called Medigap, any month of the year. But there’s one stretch of time when the answer is guaranteed to be yes, and it only comes around once for most people. (Still sorting out the cost side? Start with Medicare costs at 65.)

Your six-month window. It starts the month you’re 65 or older and enrolled in Part B. For those six months, an insurer has to sell you any Medigap plan it offers, and your health can’t be used to refuse you or raise your price.

Part B starts 1 2 3 4 5 6 Six months, no health questions any plan the insurer sells After month 6 health questions can apply

After the window. You can still apply, but the insurer can ask health questions, and in most cases it can say no or charge more based on your answers. That’s why people who skip Medigap at 65 sometimes find the door harder to open later.

If you kept working past 65. Your window doesn’t start until your Part B does. Delay Part B because you have coverage through a job, and the six months wait for you.

Colorado is kinder than most states if you’re under 65. If you qualify for Medicare early because of a disability, Colorado requires insurers to offer you Medigap during the six months after your Part B starts. You get a fresh six-month window when you turn 65 too, which is a good moment to shop again.

A few second chances. Certain events give you a guaranteed right to buy outside the window. Losing employer or retiree coverage is one. Your Advantage plan leaving your area is another. So is trying an Advantage plan when you first join Medicare and changing your mind within the first year.

One thing that confuses everybody. The fall enrollment period you see advertised every October is for Advantage and drug plans. It doesn’t reopen your Medigap window.

This is the part of Medicare where timing costs people the most, and it’s the part we watch closest as brokers. If you tell us your Part B date, we’ll tell you exactly when your window opens and closes, and compare the plans with you before it does. Our page on Medicare plans across Colorado has more on how supplements fit with the rest.

About the Author

Uncle Sheldon

Uncle Sheldon

We're the small writing team behind Uncle Sheldon Insurance. We write about insurance, but also about the local communities where we offer it. Our goal is to help readers better understand the world of insurance and their local communities.

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