Still Working at 65 in Ohio

If your employer — or your spouse’s employer — has 20 or more employees and the coverage is creditable, you can generally delay Medicare Part B past 65 without a penalty. If the employer has fewer than 20 employees, Medicare becomes your primary payer at 65 whether you enrolled or not, and delaying can leave you with large unpaid bills. Twenty is the number that decides almost everything here.

I am Steve Almeroth, an independent Medicare broker in Middleburg Heights. This is the situation I get the most calls about, and it is the one where a wrong assumption costs the most.

The 20-employee rule

Medicare calls this “coordination of benefits” — which of two insurers pays first.

Both full-time and part-time employees count toward the threshold. For a multi-employer plan, if at least one participating employer has 20 or more employees, the rules apply to everyone in the plan who is age-eligible.

Why the small-employer case is dangerous. If your company has fewer than 20 employees, Medicare is designated the primary payer the month you turn 65. If you did not enroll in Part B, there is no primary payer — and your group plan is entitled to pay only what it would have owed as the secondary payer, as though Medicare had already covered its share. Medicare’s share of a hospital stay is most of it. People discover this from a bill.

If you work for a small employer, ask your HR or benefits administrator directly: “Does this plan pay primary or secondary once I turn 65?” Get the answer in writing.

What “creditable coverage” means, and how to prove it

Delaying Part B without penalty requires coverage that Medicare recognizes as creditable — roughly, coverage at least as good as Medicare’s, through current employment.

Your plan is required to tell you. Each autumn it sends a Notice of Creditable Coverage. That notice is the document that protects you from a late-enrollment penalty years from now.

Keep every one of them. File them somewhere you will find them in a decade. When you eventually enroll, Social Security may ask you to prove you had continuous creditable coverage, and “I’m sure I did” is not proof. You will also likely need form CMS-L564, Request for Employment Information, signed by your employer, when you enroll through the Special Enrollment Period.

The 8-month Special Enrollment Period

When the employment or the coverage ends, you get a Special Enrollment Period for Part B:

• It starts the month after your Initial Enrollment Period ends.
• It ends eight months after the group health coverage ends or the employment ends — whichever happens first.

That last clause is the trap. The clock is started by the earlier of the two events, not the later one.

Coverage generally begins the first month after you sign up. If you enroll while still working, or within the first full month after employer coverage ends, you can ask to delay your Part B start date by up to three months to line it up cleanly.

A separate clock for drugs. Part D has its own rule: you have 63 days from losing creditable drug coverage to pick up a drug plan before the Part D late-enrollment penalty starts accruing. Two months, not eight. People focus on Part B and let this one slip.

Two kinds of coverage that do not count

COBRA does not count. Medicare is explicit: “COBRA isn’t considered group health plan coverage. Getting COBRA doesn’t change when this Special Enrollment Period ends.” If you leave a job in March and take 18 months of COBRA, your 8-month Part B window still started in March. It expires while you are still paying COBRA premiums, and you will not be told.

This is the most expensive mistake in this entire guide.

Retiree coverage does not count either. Neither does Marketplace coverage. The Special Enrollment Period requires coverage through current employment. Retiree benefits are, by definition, not that. Employers rarely explain this clearly at the retirement meeting — see Retiree Coverage vs Medicare in Ohio.

What about Part A?

Part A is premium-free for most people, and enrolling in it while you keep working is usually harmless.

With one significant exception: Health Savings Accounts. You cannot contribute to an HSA in any month you have any part of Medicare — including premium-free Part A. Worse, when you enroll after 65, Part A can be applied retroactively up to six months, which can turn contributions you already made into excess contributions subject to tax penalties.

If you have an HSA and intend to keep contributing, stop contributions well before you file for Medicare or Social Security, and read HSA and Medicare first. Note that claiming Social Security automatically enrolls you in Part A — you cannot take the benefit and skip the coverage.

Should you delay, even when you are allowed to?

Being permitted to delay is not the same as it being the better choice. Worth comparing:

• What your employer coverage actually costs you — premium, deductible, and out-of-pocket maximum — against Part B at $202.90/month in 2026 with a $283 annual deductible.
• Whether your employer plan is genuinely better. Some are excellent. Some high-deductible plans are worse than Original Medicare with a supplement.
• Whether you cover a spouse or dependents on that plan. This often settles it — dropping employer coverage for Medicare may leave them with nothing.
• Your income. If your modified adjusted gross income was above $109,000 (single) or $218,000 (joint) on your 2024 return, Part B costs more than the standard premium in 2026 under IRMAA.

There is no general right answer. There is a right answer for your household.

The Ohio-specific piece: your Medigap clock

If you think you may eventually want a Medicare Supplement (Medigap) policy, the timing matters more in Ohio than people expect.

Your protected Medigap window is the six months beginning the first month you are both 65 or older and enrolled in Part B — under Ohio Administrative Code Rule 3901-8-08. Inside it, no insurer can refuse you or price you on your health.

Note what that means if you delay Part B: your Medigap window does not open until Part B starts. Delaying does not waste it. But it does mean that when you finally enroll, a six-month clock starts and then closes for good — and Ohio has no “birthday rule” or annual guaranteed-issue window to fall back on. After it, supplements are medically underwritten here.

Losing employer coverage is itself a guaranteed-issue triggering event, which helps. But the clean, unconditional window is that six months.

Common questions

My spouse is still working and I’m on their plan. Same rules? Yes — the 20-employee threshold and the Special Enrollment Period both apply based on the employer providing the coverage, whether it is yours or your spouse’s.

I’m 68 and just retiring. Am I too late? No. If you had creditable coverage through current employment the whole time, you have your 8-month Special Enrollment Period and no penalty. Get the CMS-L564 signed before you lose touch with HR.

Does my employer have to tell me any of this? They must send the annual Notice of Creditable Coverage. Beyond that, benefits staff are often not Medicare experts, and the small-employer primary-payer rule in particular gets missed. Verify it yourself.

What if I already missed my window? See Missed Medicare Enrollment in Ohio — there is a General Enrollment Period, and creditable coverage during the gap can waive a penalty.

Talk it through

Bring three things and this takes one conversation: how many employees your company has, your most recent Notice of Creditable Coverage, and what your current plan costs you.

Steve Almeroth · MedStar Insurance Agency · Middleburg Heights, OH · 440-622-2112 · steve@medstar.agency

Free, no obligation. Run your dates through the calculator first if you prefer — three minutes, no email required.

Sources

• Medicare.gov — Who pays first?
• Medicare.gov — When does Medicare coverage start?
• Medicare.gov — Avoid late enrollment penalties
• CMS — Medicare Secondary Payer
• CMS — 2026 Medicare Parts A & B Premiums and Deductibles
• Ohio Administrative Code — Rule 3901-8-08, Medicare supplement

For information on all of your options, including plans I do not offer, contact Medicare.gov, call 1-800-MEDICARE, or reach Ohio’s State Health Insurance Assistance Program (OSHIIP) at 800-686-1578.