I’m Still Working At 65. Do I Need Medicare?Working Past 65 And Medicare: What To Sign Up For.

If you or your spouse still have health coverage from a job, the size of the employer and the type of coverage decide what you sign up for at 65.

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The Short Answer

If you or your spouse are still working and covered by that employer’s group health plan, you can often delay Part B without a penalty and sign up within 8 months after the job or coverage ends. At a company with fewer than 20 employees, your job-based plan might not pay without Parts A and B.

Source: Medicare.gov

Three Numbers For Working Past 65

20: The employee count Medicare.gov asks about. Below it, your job-based plan might not pay unless you have Part A and Part B.
8 Months: Your Special Enrollment Period for Part B after the job or the group coverage ends, whichever happens first.
6 Months: How far back Part A can start when you sign up after 65, which matters if you contribute to an HSA.

Which Coverage Counts

Coverage From A Current Job Versus COBRA And Retiree Plans

Medicare treats coverage from a job you still hold differently from coverage that continues after the job ends. That difference decides whether waiting costs you anything.

Question	Coverage From A Current JobYours Or Your Spouse’s	COBRA Or Retiree CoverageAfter The Job Ends
Can You Wait On Part B?	Often, yes. At an employer with fewer than 20 employees, ask the benefits office first.	Sign up when you turn 65 to avoid a coverage gap and a monthly Part B penalty.
Part A At 65	Most people pay no Part A premium, so you may want it at 65. HSA contributors should check first.	Sign up. Retiree coverage may not pay without both Part A and Part B.
Special Enrollment Period	Up to 8 months after the job or the group coverage ends, whichever happens first.	COBRA doesn’t extend it. The 8 months start when you stop working.
Drug Coverage	If your plan’s drug coverage is creditable, you can wait to join a Medicare drug plan.	The same test applies. Avoid going 63 days or more without creditable drug coverage.
Paperwork	Form CMS-L564, filled out by the employer, shows you had job-based coverage.	Your regular application through Social Security when you turn 65.

Self-employed, or unsure your plan counts as employer group coverage? Medicare.gov says to ask your insurer, and to sign up at 65 if it doesn’t qualify.

Do I Need To Sign Up For Medicare At 65 If I Have Insurance At Work?

Sometimes, and the answer turns on where the coverage comes from. If you or your spouse are still working and the group health plan comes from that job, Medicare.gov says you may be able to wait to sign up for Part B without paying a late enrollment penalty. You then sign up once the work or the coverage stops.

Employer size changes the picture. Medicare.gov’s enrollment questions ask whether the employer has 20 or more employees. When it has fewer, your job-based coverage might not pay for health services unless you have both Part A and Part B, so talk to the benefits office before your 65th birthday month.

Should I Take Part A Even If I Keep My Job’s Plan?

For most people Part A carries no premium, because they or a spouse paid Medicare taxes long enough, generally at least 10 years. Medicare.gov says that is why you may want to sign up for Part A at 65 even while you or your spouse keep working, and wait on Part B, which costs $202.90 a month in 2026 for most people.

One group should pause first: people who contribute to a Health Savings Account. Medicare enrollment of any kind changes what you can put into an HSA, and Part A can reach back in time when you sign up. The next question covers how that works.

What Happens To My HSA When I Sign Up For Medicare?

The IRS says that beginning with the first month you are enrolled in Medicare, your HSA contribution limit is zero, and the rule applies to retroactive coverage too. That matters because Part A can start up to 6 months before the month you sign up, though never before the month you turned 65.

Claiming Social Security after 65 also enrolls you in Part A automatically. So Medicare.gov advises that you and your employer stop contributing to your HSA 6 months before you retire or apply for Social Security benefits, to avoid a tax penalty. Your CPA can confirm the timing for your own contributions.

How Do I Sign Up For Part B When I Stop Working?

You use your 8-month Special Enrollment Period. If you already have Part A, you apply for Part B online at Social Security and send form CMS-L564, which your employer fills out to show you had job-based coverage. If the employer can’t complete it, you complete Section B as fully as you can, leave it unsigned and include proof of your coverage.

Timing the start date avoids a gap. Medicare.gov says to sign up the month before you retire if you want Medicare to begin when the employer plan ends. If you sign up while still working, or within the first full month after the coverage ends, you can ask to delay your Part B start date up to 3 months.

What If I Retire And Take COBRA?

COBRA keeps your old plan going, but Medicare treats it differently from coverage through a current job. Your 8-month window to sign up for Part B starts when you stop working, even if you choose COBRA, and getting COBRA doesn’t change when that window ends.

If you haven’t signed up for Medicare yet, Medicare.gov says to sign up when you turn 65 to avoid gaps in coverage and a Part B penalty, and warns against waiting for COBRA to run out. Your COBRA coverage will probably end once you sign up. If you already had Medicare when you got COBRA, Medicare generally pays first and COBRA pays after it.

What About Medigap And Drug Coverage When I Finally Retire?

Your one-time, 6-month Medigap Open Enrollment Period begins when you sign up for Part B, even if you sign up while you still have employer coverage. Medicare.gov points out that employer coverage often works much like Medigap, so taking Part B early can use up that window before you need it.

For drugs, you can wait to join a Medicare drug plan as long as your current coverage is creditable, and you avoid the Part D penalty by never going 63 days or more without creditable coverage. Your plan has to tell you whether it qualifies. Maartin can line these dates up with your retirement date by phone, by Zoom or at his Riverside office.

Next Step

Talk It Through

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Questions

Common Questions

Written by Maartin Rossouw, President, MJR Financial & Insurance Services. CA Insurance License #790783. Facts from Medicare.gov and IRS.gov. Updated October 28, 2026 · 6 Min Read.

Does COBRA count as employer coverage for Medicare?

No. Medicare.gov says COBRA isn’t considered group health plan coverage for the Special Enrollment Period, and getting COBRA doesn’t change when that period ends.

What if my spouse is the one still working?

Coverage through your spouse’s current job works the same way. If their employer’s group health plan covers you, you may be able to delay Part B and use the 8-month Special Enrollment Period after their job or the coverage ends.

Is retiree health coverage enough to skip Part B?

Usually not. Medicare.gov says retiree coverage may not pay for your care unless you have both Part A and Part B, and once you retire Medicare generally pays first. Ask your benefits administrator before you join any plan, so you keep the retiree coverage.

What if I’m self-employed?

Ask your insurer whether your coverage counts as employer group health plan coverage as the IRS defines it. If it doesn’t, Medicare.gov says to sign up when you turn 65 to avoid a monthly Part B late enrollment penalty.

Can I keep contributing to my HSA after 65?

Only until you enroll in Medicare. The IRS sets your contribution limit at zero starting with the first month of Medicare enrollment, including months of retroactive Part A coverage.

Sources

Medicare Disclaimer

We do not offer every plan available in your area. Currently we represent 6 organizations which offer 87 products 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 affiliated with or endorsed by the U.S. government or the federal Medicare program.

Please Note

Education, not advice. MJR Financial & Insurance Services does not give tax, legal or Social Security advice; please consult your own professionals.

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