When do I sign up for Medicare if I'm turning 65?

During your Initial Enrollment Period, the seven months that run from three months before the month you turn 65 through three months after. Sign up in the three months before your birthday so your coverage starts on time with no gap.

Do I have to enroll at 65 if I'm still working?

Not always. If you work for an employer with 20 or more employees and have creditable group coverage, you can usually delay Part B without penalty and enroll later through a Special Enrollment Period. If your employer has fewer than 20 employees, or you have no other coverage, you should enroll on time. COBRA and retiree plans do not count for delaying Part B.

What happens if I miss my enrollment window?

You can face lifelong late penalties. Part B adds 10% for each full 12 months you could have had it but didn't, and Part D adds 1% per month without creditable drug coverage. You may also have a gap before your coverage can start.

Should I choose a Medigap supplement or a Medicare Advantage plan?

Both are valid, and the right answer depends on you. A Medigap supplement plus a Part D plan gives you nationwide provider freedom and predictable costs; a Medicare Advantage plan bundles everything through a network, often with extra benefits. Remember your one-time six-month Medigap Open Enrollment window, when a supplement is guaranteed regardless of your health.

How do I actually sign up for Medicare?

Through Social Security, either online at ssa.gov, by phone at 1-800-772-1213, or at a local office. If you're already receiving Social Security benefits before 65, you're enrolled in Part A and Part B automatically.

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Turning 65

Turning 65? Your Step-by-Step Medicare Roadmap

Austin TylerLocal Kentucky Medicare agent · July 17, 2026 · 8 min read

Turning 65 is a big milestone, and it comes with a Medicare deadline you really don't want to miss. I walk Kentuckians through this every week, and here's the good news: once you see the steps laid out in order, it's a lot simpler than it looks. Here's your roadmap for what to do, so you start on the right coverage and avoid the penalties that can follow you for the rest of your life.

Step 1Know your seven-month window

Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, your birthday month, and the three months after. Here's a tip worth real money: enroll during the three months before your birthday, so your coverage starts the month you turn 65 with no gap. I break the timing down day by day in The 7-Month Window: When to Sign Up for Medicare.

Step 2Decide whether to enroll now or wait

Not everyone signs up right at 65. The question is whether you already have coverage that counts:

If you have no other coverage (or your employer has fewer than 20 employees), enroll on time. Medicare will be your primary coverage.
If you're still working at an employer with 20 or more employees and have solid group coverage, you may be able to delay Part B without penalty and enroll later through a Special Enrollment Period. Confirm in writing that your plan is "creditable." I cover this in Still Working at 65? What to Do About Medicare.
Watch two traps. COBRA and retiree coverage do not let you delay Part B without penalty. And if you contribute to a Health Savings Account (HSA), enrolling in any part of Medicare (including Part A) stops your HSA contributions.

Step 3Understand Part A and Part B

Original Medicare has two parts. Part A (hospital) is usually premium-free if you or your spouse worked and paid Medicare taxes for about 10 years. Part B (doctors and outpatient care) has a monthly premium, which is $202.90 as the standard amount in 2026. If you already receive Social Security, you're enrolled automatically at 65. If not, you sign up through Social Security at ssa.gov or 1-800-772-1213.

Step 4Choose your coverage path

This is the big decision, and there are two roads:

Original Medicare plus a Medigap supplement plus a stand-alone Part D drug plan. You get the freedom to see any provider in the country that takes Medicare, with predictable costs.
A Medicare Advantage plan, which bundles everything (usually including drug coverage and extras) through a private plan that uses a network.

I compare the two roads honestly in Medicare Advantage vs. Medigap: The Real Difference.

Don't miss this window.When you're 65 and enrolled in Part B, you get a six-month Medigap Open Enrollment Period. During it, a supplement company must sell you a policy regardless of your health history. Miss it, and buying a supplement later in Kentucky can require medical underwriting, where you can be charged more or turned down. It's one of the most valuable windows in all of Medicare, so use it if a supplement is your path.

Step 5Don't skip drug coverage

Even if you take no medications today, going without creditable drug coverage triggers a lifelong Part D late penalty. A lot of healthy people enroll in a low-cost plan simply to avoid the penalty and to be covered the day a prescription does come up. Here's how drug plans work: Medicare Part D Explained.

Step 6Get a second set of eyes before you enroll

You don't have to make these choices alone, and you shouldn't have to. A local, independent advisor can look at your doctors, your medications, and your budget, compare your options, and make sure you don't trip a penalty or miss the Medigap window. It's free, and it's the difference between guessing and knowing. Here's what to look for: What a Medicare Advisor Really Is.

The four mistakes that cost people the most.Missing your seven-month window (a lifelong penalty), assuming COBRA lets you delay Part B (it doesn't), contributing to an HSA after you enroll in Medicare, and letting your six-month Medigap window close.

Turning 65 soon? You can get a free Medicare review. I'm local, independent, and there's no cost and no pressure. I'll walk you through every step and make sure you start on the right plan.

Quick recap

Your Initial Enrollment Period is seven months: three months before your birthday month, that month, and three months after.

If you don't have creditable coverage, enroll on time. COBRA and retiree coverage do not let you delay Part B.

Part A is usually premium-free; Part B has a monthly premium ($202.90 standard in 2026). Sign up through Social Security.

Choose your path: Original Medicare with a supplement and drug plan, or a Medicare Advantage plan.

Use your six-month Medigap window and add Part D drug coverage, even if you're healthy, to avoid penalties.

Test what you learned

Five quick questions. Pick an answer to see if you're right, and why.

Let's map out your Medicare together.

I'm a local, independent Kentucky agent. No call center, no pressure, no cost, just clear guidance that gets you started on the right plan, with the penalties avoided.

Get my free review →

Or call me directly: (859) 618-6443

This article is general information, not advice for your specific situation, and Medicare rules and figures change every year. 2026 figures are from CMS. Tyler Insurance Group is not connected with or endorsed by the U.S. government or the federal Medicare program. We do not offer every plan available in your area. For complete details, contact Medicare.gov or 1-800-MEDICARE.