Washington-Specific

Medicare and Still Working at 65: What Washington Residents Need to Know

By Michael Gurr · Published 2026-05-12 · Updated 2026-05-12

Most people approaching 65 with employer coverage assume they can simply wait on Medicare. Sometimes that's right. Sometimes it's a mistake that adds a permanent penalty to every Medicare bill for the rest of their life.

Whether you can safely delay Medicare while still working comes down to one question: how many employees does your company have?

Does the Size of Your Employer Actually Matter?

Yes — and it's the single most important factor in this decision.

If your employer has 20 or more employees, your employer plan is considered primary coverage. Medicare is secondary. You can delay enrolling in Medicare Part B without penalty, and you'll have a Special Enrollment Period when your employer coverage eventually ends.

If your employer has fewer than 20 employees, Medicare becomes your primary coverage at 65 — whether you enroll or not. Your small employer plan becomes secondary. If you don't enroll in Part B when you're eligible, you're exposed to both the late enrollment penalty and potential gaps in coverage that your employer plan won't fill. You'll need to enroll during your Initial Enrollment Period to avoid these issues.

What this means in clear terms: "I'm covered through work" is not enough information. The size of your company changes your entire Medicare obligation.

What Counts as Qualifying Employer Coverage?

Not all coverage protects you from Medicare penalties. This is where a lot of Washington residents get tripped up.

Coverage that qualifies (lets you delay penalty-free):

Active employer-sponsored health insurance through a company with 20+ employees
Coverage through a spouse's employer, if that employer has 20+ employees

Coverage that does NOT qualify:

COBRA continuation coverage
Retiree health coverage from a former employer
Coverage through a marketplace plan (ACA)
Coverage through a small employer (under 20 employees)
VA benefits (for Medicare purposes)

If you left a job and kept coverage through COBRA, you are not protected from penalties. COBRA is not considered qualifying employer coverage under Medicare's rules. Many people don't find this out until they try to enroll — and by then the penalty clock has already been running.

What this means in clear terms: If your coverage is through COBRA, a retiree plan, or a small employer, you may already owe a late enrollment penalty. The sooner you sort this out, the better.

Can You Enroll in Part A Without Part B?

For most people, yes — and it often makes sense.

Medicare Part A (hospital coverage) is free for anyone who has worked and paid Medicare taxes for at least 10 years. There's no premium, so there's generally no reason to delay it.

Part B is where the decision gets complicated. Part B has a monthly premium ($202.90 in 2026 for most people) and carries the late enrollment penalty if you delay without qualifying coverage. Part B is what most people are weighing when they ask this question.

You can enroll in Part A alone while staying on employer coverage for Part B — that's a common and legitimate approach when your employer has 20+ employees. Just know the Part A deductible ($1,676 per benefit period in 2026) still applies.

One Thing Most People Miss: The HSA Rule

If you're contributing to a Health Savings Account (HSA) through your employer, enrolling in any part of Medicare — including Part A — stops your eligibility to contribute.

More importantly: Medicare Part A coverage is retroactive up to 6 months if you enroll late. That means if you enroll at 67, your Part A coverage backdates to when you were 66½. Any HSA contributions you made during that retroactive window are considered excess contributions by the IRS and subject to penalty.

If you're planning to delay Medicare and keep contributing to your HSA, stop contributions at least 6 months before you plan to enroll in Medicare. Work with your benefits administrator to confirm the timing.

What this means in clear terms: Don't assume your HSA and Medicare can coexist seamlessly. They can't — and getting this wrong creates a tax problem on top of a Medicare problem.

What Happens When Your Employer Coverage Ends?

When you leave your job or your employer coverage ends, you enter a Special Enrollment Period (SEP). This gives you 8 months to enroll in Medicare Part B without penalty.

A few important details:

The 8-month window starts the day after your employer coverage ends — not when COBRA begins
It does not restart if you pick up COBRA — the 8-month clock runs regardless
If you miss the 8-month window, you'll need to wait for the General Enrollment Period (January 1–March 31), with coverage starting July 1, and you'll owe the late penalty

If you're within 3 months of retirement, start the Medicare enrollment process now so there's no gap in coverage.

A Quick Decision Framework for Washington Residents

Your Situation	What to Do
Working, employer has 20+ employees	Part A optional (usually enroll). Delay Part B until coverage ends.
Working, employer has fewer than 20 employees	Enroll in both Part A and Part B at 65.
On COBRA	Enroll in Medicare — COBRA does not protect from penalties.
On a spouse's large employer plan	Can delay penalty-free. Confirm employer size first.
On a spouse's small employer plan	Enroll in Medicare at 65.
Retired with retiree health coverage	Enroll in Medicare — retiree plans do not qualify as creditable coverage for delay.

Frequently Asked Questions

Can I delay Medicare if I'm still working and have employer coverage at 65?

Yes, if you work for a company with 20 or more employees and are covered by that employer's health plan through your own active employment. You can delay Part B without penalty until you retire or lose that coverage.

What if my employer has fewer than 20 employees?

If your employer has fewer than 20 employees, Medicare becomes your primary insurance at 65 — even if you're still working. Your employer plan becomes secondary. You should enroll in Medicare Part B during your Initial Enrollment Period to avoid gaps and penalties.

Does my spouse's employer coverage let me delay Medicare?

It depends on the employer size. If your spouse works for a company with 20 or more employees and you are covered under their plan, you may be able to delay Medicare. Coverage through a small employer (under 20 employees) does not protect you from the late enrollment penalty.

How long do I have to enroll in Medicare after I retire?

You have a Special Enrollment Period of 8 months from the date your employer coverage ends or you stop working — whichever comes first. Do not wait for COBRA to run out — the 8-month window starts when active employer coverage ends, not when COBRA ends.

If you're approaching 65 and still working, the stakes are real — but the decision is manageable once you know the rules. I'm happy to look at your specific situation and tell you exactly what to do and when.

Have questions about your specific situation?

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Michael Gurr is a licensed Medicare and retirement advisor serving Pierce County and Washington State.

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This article is for educational purposes. For official Medicare information, visit medicare.gov.