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:
- The size of your employer
- The type of health coverage you have
- Whether you’re on your plan or a spouse’s
- 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 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.
- 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.
- If your employer has fewer than 20 employees: Medicare becomes primary, 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 at 65, even while still working, because:
- It’s usually premium-free if you worked and paid Medicare taxes for 10+ years
- 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
Part B has a monthly premium, so many people try to delay it. 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% premium penalty for each full year of delay, applied for life.
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:
- COBRA drug coverage can be creditable, but you must confirm it in writing.
- If your COBRA drug coverage ends, you have 63 days to enroll in a Part D plan to avoid a penalty.
- 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:
- The employer size of your spouse’s company
- Whether it’s active employment-based coverage
- Whether both medical and drug coverage are creditable
Situations That Create Confusion
- 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.
- Retiree coverage is not active employment-based coverage, so it won’t delay Medicare requirements.
- Self-employed individuals without group insurance from a company with 20+ employees usually need to enroll in Medicare at 65.
So… Do I Need to Enroll or Not?
There’s no universal answer. And that’s why so many people get this wrong.
If you delay enrollment and assume you’re covered, you could get hit with:
- Denied claims if Medicare should’ve been primary
- Permanent late penalties for both Part B and Part D
- Gaps in coverage you can’t fix immediately
That’s why we always recommend verifying your situation with a professional who actually understands Medicare—not just a benefits brochure or online form.
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.