Turning 65 guide

Turning 65 and Medicare: A Step-by-Step Enrollment Guide

By Maxwell Kingsbury, licensed independent insurance agent · Last updated October 2026

Turning 65 is the usual time to start Medicare, and the rules around it are stricter than most people expect. Enroll on time and you avoid penalties. Miss your window and some of those penalties last for life. This guide walks you through the timeline, the steps, and the special rules if you're still working.

It's written for people turning 65 who are new to Medicare. If you're already enrolled and want to change plans, see our guides to Medicare Advantage, Medigap and Part D.

Your Medicare Timeline

Your first chance to sign up is called your Initial Enrollment Period. It lasts seven months and is built around your 65th birthday.

About 6 months before you turn 65: get your bearings

Learn what the four parts of Medicare cover, which our Medicare 101 guide explains in plain English. Make a list of your doctors and your prescriptions. Find out whether you will get Social Security benefits, and whether you or your spouse still have job-based coverage.

3 months before your birthday month: your window opens

Your seven-month window starts three months before the month you turn 65. It includes your birthday month and ends three months after it. If you sign up in the first three months, your coverage can start the first day of your birthday month.

Tip: If your birthday is on the first day of the month, Medicare starts the month before. Check your exact dates on Medicare.gov or with Social Security.

Your birthday month and the 3 months after

You can still enroll, but coverage starts later. If you sign up in your birthday month or after, your coverage generally starts the month after you enroll, which can leave a gap if you've lost other coverage.

After the window closes

If you miss your window and don't have qualifying job-based coverage, you may have to wait for the General Enrollment Period (January 1 to March 31). Your coverage then starts the month after you sign up. For Part B, you may also pay a late-enrollment penalty: 10% more for each full 12 months you could have had Part B but didn't, for as long as you have it.

Watch out: The Part B penalty is permanent. It is added to your premium every month you have Part B, so a missed window can cost you for life.

Step-by-Step: What to Do

Step 1: Find out if you'll be enrolled automatically

If you already receive Social Security or Railroad Retirement benefits at least four months before you turn 65, you're usually signed up for Medicare Parts A and B automatically, and your Medicare card arrives in the mail about three months before your birthday. If you don't receive those benefits yet, you need to sign up yourself.

Step 2: Check whether you have other coverage

Do you or your spouse still work and have a group health plan through that job? This affects whether you should take Part B now. We cover this in If You're Still Working at 65 below. Coverage through COBRA or retiree plans is treated differently from active job-based coverage, so check before you delay anything.

Step 3: Sign up for Part A and Part B

If you aren't enrolled automatically, you can sign up for Parts A and B online with the Social Security Administration at SSA.gov/medicare/sign-up (opens in a new tab), or call 1-800-772-1213. Part A is premium-free for most people who worked and paid Medicare taxes for about 10 years. Part B has a monthly premium. The standard Part B premium was $202.90 a month in 2026, and the 2027 amount is usually announced in November.

Step 4: Choose how you want to get your coverage

Most people choose between two paths. Neither is right for everyone.

Tip: Medigap has a six-month Medigap Open Enrollment Period that starts the month you are 65 or older and enrolled in Part B. During that time, insurers can't turn you down or charge more for health reasons. Later, they can ask health questions in most cases. So the month your Part B starts matters.

Step 5: Add drug coverage

If you choose Original Medicare, you'll want a standalone Part D plan. If you go without drug coverage that is at least as good as Medicare's for 63 days or more, a late-enrollment penalty can be added to your Part D premium for as long as you have it. Our Part D guide walks through comparing plans step by step.

Step 6: Check your doctors and your prescriptions

Before you choose a plan, check that your doctors and hospital are covered, and that your medications are on the plan's drug list. Medicare Advantage plans use networks. Original Medicare with Medigap does not.

Step 7: Enroll, and keep your confirmation

Enroll in your plan through the plan, Medicare.gov, 1-800-MEDICARE or an agent. Keep your confirmation and your new member ID card, and make sure your start date matches the date your other coverage ends.

Would you like help with your first Medicare choices?

There is no charge for our help. Tell me when your birthday is, whether you're still working, and which doctors and drugs matter to you, and I'll walk you through your options. A plan costs the same whichever way you enroll.

Request a call Call 727-351-3321

If You're Still Working at 65

You don't always have to take Part B at 65. It depends on your coverage.

Watch out: If you have a health savings account (HSA), you can't contribute once you are enrolled in Medicare, and Part A can reach back up to six months when you enroll after 65. Many people stop contributing about six months before they sign up. Ask your benefits administrator or a tax advisor.

Rules differ by company size and plan type, so ask your HR department before you decide. We can also help you work through it.

Common Mistakes to Avoid

FAQs

Do I have to sign up for Medicare at 65?

Not always. If you have qualifying coverage through active work, you may be able to wait without a penalty. If you don't, you generally should sign up during your Initial Enrollment Period. If you take Social Security, Part A starts automatically.

Will I get my Medicare card automatically?

If you already receive Social Security or Railroad Retirement benefits, usually yes, about three months before you turn 65. Otherwise you sign up yourself.

How much does Medicare cost?

Part A is premium-free for most people. Part B has a monthly premium that is higher for people with higher incomes. Drug plans and Medicare Advantage plans have their own premiums, and some have $0 plan premiums. You may also pay deductibles, copays and coinsurance.

Can I keep my employer plan and have Medicare?

Yes. Many people do. How the two work together depends on your employer's size and on which one pays first. Ask your benefits administrator.

When should I start looking at plans?

About six months before you turn 65. That gives you time to learn your options before your window opens.

Official Sources

Related Guides

Disclaimer. This guide is educational and is not medical, legal or tax advice. Medicare rules change, and your situation may differ, so confirm your dates and options with Social Security, Medicare or your benefits administrator. Maxwell Kingsbury is a licensed independent insurance agent (Florida License # G365332, NPN 22312975) and is compensated by insurance carriers. We do not offer every plan available in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options. Not connected with or endorsed by the U.S. government or the federal Medicare program.
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