More and more people are working past 65—by choice or necessity. But what most don’t realize is that your employment status doesn’t automatically delay Medicare requirements.
Whether or not you need to enroll in Medicare at 65 depends on several key factors:
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The size of your employer
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The type of health coverage you have
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Whether you’re on your plan or a spouse’s
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And which parts of Medicare we’re talking about (Parts A, B, and D follow different rules)
This post walks you through what to consider, so you can avoid costly penalties or coverage gaps.
Medicare, Employer Coverage, And Employer Size: Why 20 Is The Magic Number
The first thing to know is that Medicare rules change depending on the size of your (or your spouse’s) employer.
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If your employer has 20 or more employees: You can usually delay Medicare Part B and Part D without penalty as long as your coverage is creditable. In this case, Medicare typically acts as a secondary payer to your employer coverage.
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If your employer has fewer than 20 employees: Medicare becomes your primary coverage, and you typically must enroll in Medicare at age 65—even if you have group insurance.
If you work for a small business or are covered under a spouse’s small employer plan, failing to enroll in Medicare could result in denied claims and late enrollment penalties.
Part A: Should You Enroll If You’re Still Working?
Most people enroll in Medicare Part A, also known as hospital insurance, at 65, even while still working, because:
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It’s usually premium free and is part of Original Medicare. If you worked and paid payroll taxes for 10+ years that makes you eligible for premium-free Part A coverage.
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It may act as secondary coverage for hospital stays.
But be careful if you have an HSA. Once you enroll in any part of Medicare, you can no longer contribute to your Health Savings Account, and neither can your employer. You may want to delay Part A if HSA contributions are important to you.
Part B: This Is Where Most Mistakes Happen
Medicare Part B has monthly premiums, so many people try to delay enrollment. That’s fine, but only if your employer-based coverage qualifies as creditable and your employer has 20 or more employees.
If you’re working for a small employer, or on COBRA, you typically must enroll in Part B when first eligible, or face a 10% penalty on your Part B premiums for each full year of delay, applied for life. Part B coverage includes outpatient care, preventive services, and other medical services not covered by Part A.
Part D: Prescription Drug Coverage Has A Stricter Clock
To avoid the Part D penalty, you need to maintain creditable drug coverage—meaning it’s at least as good as Medicare’s standard.
If your employer or union plan (or COBRA drug coverage) is creditable, you can delay Part D.
Here’s The Catch With COBRA:
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COBRA drug coverage can be creditable, but you must confirm it in writing.
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If your COBRA drug coverage ends, you have 63 days to enroll in a Part D plan to avoid a penalty.
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If your COBRA drug coverage is not considered creditable, you need to enroll in Part D when first eligible to avoid lifetime penalties.
What About Spouse Coverage?
If you’re on your spouse’s group insurance, the same rules apply. Medicare considers:
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The employer size of your spouse’s company
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Whether it’s active employment-based coverage
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Whether both medical and drug coverage are creditable
Situations That Create Confusion
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COBRA coverage is not considered creditable for Part B. If you’re 65+ and relying on COBRA for medical coverage, you’ll need to enroll in Part B to avoid penalties and gaps. When your employer coverage ends, you may qualify for a special enrollment period to sign up for Medicare without penalty.
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Retiree coverage is not active employment-based coverage, so it won’t delay Medicare requirements. Missing the appropriate enrollment periods can result in penalties.
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Self-employed individuals without group insurance from a company with 20+ employees usually need to enroll in Medicare at 65. Missing enrollment periods can also lead to penalties.
So… Do I Need To Enroll Or Not?
There’s no universal answer to when you need to sign up for Medicare if you’re working past 65. And that’s why so many people get this wrong.
If you delay enrolling or are considering delaying Medicare, you could get hit with:
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Denied claims if Medicare should’ve been primary
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Permanent late enrollment penalty for both Part B and Part D, which can last for twice the number of years you delayed enrolling
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Gaps in coverage you can’t fix immediately
Additionally, failing to stop HSA contributions before enrolling in Medicare can result in a tax penalty.
That’s why we always recommend verifying your situation with a professional who actually understands Medicare—not just a benefits brochure or online form.
FAQs
Do I have to enroll in Medicare at age 65 if I’m still working?
It depends. If you work for an employer with 20 or more employees and have creditable coverage, you may be able to delay Medicare Part B and Part D without penalty. But if your employer has fewer than 20 employees, Medicare may become your primary coverage, and you’ll generally need to enroll when first eligible.
What is creditable coverage, and why does it matter?
Creditable coverage means your employer or group health plan offers benefits at least as good as Medicare’s standard. If your plan is creditable, you may delay Parts B or D without penalty. If not, delaying enrollment could trigger lifelong penalties.
Can I delay Medicare Part A if I’m still working?
Often people enroll in Part A because it’s premium-free for many. However, one reason to delay it is if you’re contributing to a Health Savings Account (HSA), because once you enroll in any part of Medicare you can no longer make HSA contributions.
Does COBRA count as creditable coverage for Medicare?
COBRA is not creditable for Medicare Part B. You can’t use COBRA to delay Part B without penalty. However, COBRA can be creditable for Part D (prescription drug coverage) if it meets standards, but you have to verify that. If your COBRA drug coverage ends, you have a 63-day window to enroll in Medicare Part D to avoid a penalty.
How can I avoid penalties or coverage gaps?
Make sure you understand whether your employer’s coverage is creditable, know the employer size rules, time your Medicare enrolments correctly, keep good documentation (especially proof of creditable coverage), and consult a professional who’s familiar with Medicare rules.
Need Help Making The Right Call?
At Brickhouse, we help people figure this out every day. Whether you’re actively working, on COBRA, covered through your spouse, or preparing to retire—we’ll walk you through what applies to you.
Click here to schedule a free consultation with Niki or a member of our team. There’s no cost and no obligation to enroll.
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Written by Niki Feret
Licensed Independent Medicare Insurance Agent
Founder, Brickhouse Agency & Chicagoland Medicare
As a female agency owner in a space that’s often dominated by call centers and cookie-cutter advice, I started Brickhouse to do things differently.
We’re a boutique Medicare agency—real people helping real people. No scripts, no pressure, and no one-size-fits-all recommendations. Just thoughtful, personalized guidance that helps you make confident Medicare decisions. If you’re ready to feel supported—not sold—
Schedule a free consultation here. There’s no cost and no obligation to enroll. Ever.
