Medicare & Employer Coverage

New to Medicare · Still Working

Medicare & employer coverage.

Turning 65 but still working — or covered by a spouse’s plan? Whether you should take Medicare now or delay it depends on a few key details. Here’s how to get it right and avoid a lifelong penalty.

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The Short Version

The one detail that changes everything: employer size.

When you’re still working at 65, the big question is whether to enroll in Part B now or delay it. The answer usually hinges on how many employees your (or your spouse’s) employer has — because that determines whether Medicare or your employer plan pays first.

Get this right and you keep great coverage while avoiding wasted premiums. Get it wrong and you can face a Part B late penalty for the rest of your life, or a gap in coverage. Most people benefit from a quick, free conversation before deciding — the rules have real traps.

New to the basics? Start with What is Medicare, check Medicare Eligibility, or read the full Medicare 101 guide.
Interactive · Employer Size

How big is your employer?

This is the detail that usually decides whether to take Part B now or delay. Pick the one that fits — a licensed advisor confirms your specifics for free.

The employer providing your health plan has:
Count the employer of whoever’s plan covers you (yours or your spouse’s).
You can often delay Part B — safely.

With 20+ employees, your employer group plan generally pays first and Medicare second. Many people keep Part A (it’s usually free) and delay Part B without penalty, then enroll later during a Special Enrollment Period when they leave the job. We’ll confirm your plan is truly creditable first.

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You likely need to enroll in Part B now.

With fewer than 20 employees, Medicare usually pays first — which means you generally should take Part B at 65, or your small-employer plan may pay very little and leave you exposed. Delaying here can be a costly mistake. Let’s make sure you’re covered correctly.

See How to Apply
Important: COBRA and retiree plans are different.

COBRA and retiree coverage do NOT count as active employer coverage for delaying Part B. If you’re relying on these, you usually need to enroll in Medicare on time anyway — or risk a penalty and a coverage gap. This trips up a lot of people. Let’s sort out your timing.

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The Two Choices

Keep your plan, or move to Medicare?

When you’re working past 65, it usually comes down to these two paths. The right one depends on your coverage, costs, and employer size.

Keep employer coverage, delay Part B

Common when the employer has 20+ employees
  • ✓Usually take premium-free Part A anyway
  • ✓Delay Part B to avoid paying for coverage you don’t need yet
  • ✓Enroll later during your Special Enrollment Period — penalty-free
  • ✓You’ll need the CMS-L564 employer form when you do

Move to Medicare now

Common with small employers, or when Medicare is cheaper/better
  • ✓Take Parts A and B at 65
  • ✓Add a Supplement + drug plan or a Medicare Advantage plan
  • ✓Often lower cost than an employer plan for one person
  • ✓We compare your employer plan against Medicare, side by side
Compare My Options How to Choose a Plan

Working past 65? Don’t guess on this one.

The employer-coverage rules have real penalties for getting them wrong. One free conversation and you’ll know exactly what to do.

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Keep Going

What to look at next.

Once you know your employer-coverage path, here’s where to head.

Sign Up

How to Apply for Medicare

Includes the CMS-L564 employer form you’ll need for a penalty-free Special Enrollment Period.

How to apply 
Timing

Enrollment Periods

Understand your Special Enrollment Period so you switch to Medicare without a penalty.

See the windows 
Compare Costs

Medicare Costs

See what Medicare costs so you can compare it fairly against your employer plan.

Understand costs 
Quick Answers

Working-past-65 questions.

Do I have to enroll in Medicare at 65 if I’m still working?
Not always. If your employer has 20+ employees, you can often keep that coverage and delay Part B without penalty, enrolling later during a Special Enrollment Period. If the employer has fewer than 20, you usually should take Part B at 65. Most people should still take premium-free Part A.
What happens if I don’t sign up for Part B and I should have?
You could face a lifelong Part B late enrollment penalty — an amount added to your premium permanently — plus a possible gap in coverage. That’s why confirming your situation before deciding is so important.
Does COBRA or retiree coverage let me delay Part B?
No. COBRA and retiree coverage do not count as active employer coverage for delaying Part B. If you’re relying on them, you generally need to enroll in Medicare on time to avoid a penalty. This is a common and costly misunderstanding.
Can I have both Medicare and my employer plan?
Yes — many people do. One pays first (the “primary”) and the other pays second. Which is primary depends mainly on employer size. We’ll help you understand how they’d coordinate for you, and whether keeping both makes sense.
What’s the CMS-L564 form?
It’s the Request for Employment Information form — proof of your employer coverage that lets you enroll in Part B during a Special Enrollment Period without a penalty when you leave the job. Your employer completes part of it. You can download it on our How to Apply page.

Let’s make sure you time this exactly right.

A licensed May River advisor compares your employer plan against Medicare and confirms your timing — free, and with no pressure.

(843) 227-6725
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