Real questions from real calls : and the reasoning behind the answers.
This is one of the most common calls I get, and it shows up in almost the same shape every time. Someone who just turned 65, or is about to, tells me: “My biggest question is right now, I’m working, and I’m going to be 65 at the end of November. I’m still working, and I have good health insurance. So how did I delay that?”
Sometimes it comes from someone further out, working the math on a retirement date that’s still years away:
“let’s say my plan is to basically retire at 67 for my full retirement, but then continue to work… do I have to sign up if I could still get it under the company I’m working for?”
And underneath almost every version of this question, there’s a rumor doing the driving — something heard secondhand, half-remembered from a coworker: “Someone’s telling me that if you have health insurance but you’re working, you don’t have to worry about this quite yet.”
That rumor isn’t wrong. It’s just incomplete. Whether you have to take Medicare at 65 while you’re still working depends on one number almost nobody asks about first — how many people work at your company.
Grab a time and I will tell you straight which path fits : and which does not.
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Do you have to take Medicare at 65 if you’re still working?
The short version: it depends on the size of your employer, not your age.
If your company has 20 or more employees, the group health plan is usually considered primary — meaning it pays your claims first, before Medicare would. In that situation you can generally delay both Part A and Part B without penalty, for as long as you keep that coverage. When the job ends, or you decide to retire, there’s a set window afterward to enroll without being treated as late.
If your company has fewer than 20 employees, Medicare typically becomes primary the day you turn 65 — whether you’ve enrolled or not. Delaying in that case isn’t free. Claims can go unpaid the way the employer plan expects, because it’s assuming Medicare already covered its share first.
The word that decides all of this is creditable — meaning your employer coverage is considered at least as good as Medicare’s. I ask people to get that confirmed by HR in writing before we plan around it, because the answer isn’t always obvious from the outside. One caller described the exact confusion this creates:
“That’s not laid out anywhere. That’s kind of confusing because if you look on the Medicare site, it says you’ve got this deadline and you’ve got to sign up. It doesn’t say creditable coverage, or maybe it does in the fine print.”
She’s right that it’s buried. The deadline language is written for people with no other coverage. If you have coverage, the rules bend — but only if it actually qualifies.
What I ask before I’d ever tell you to wait
Before I tell anyone to delay or to enroll, I ask a handful of questions. They sound simple, but the answers usually decide the entire conversation.
- How many employees does your company have? This is the first fork in the road. Twenty is the number that changes everything downstream.
- Has HR confirmed your coverage is creditable? Not “good insurance” in a general sense — specifically as good as Medicare’s, and in writing.
- Do you have a Health Savings Account, and are you still contributing to it? This one catches more people off guard than any other question on this list.
- Is anyone else covered on your plan who isn’t 65 yet? A spouse or domestic partner under 65 generally can’t ride along on your Medicare and needs coverage of their own.
- When do you actually plan to stop working? Not the wished-for date — the real one. It changes how far ahead we need to start any paperwork.
- What does your health look like right now, and what’s in your family history? Delaying is often the right move on paper. It’s a different conversation when there’s a condition that makes “later” a real gamble.
The HSA question deserves its own moment, because it trips people up quietly. Enrolling in any part of Medicare — even zero-premium Part A — stops you from contributing to a Health Savings Account going forward, and Part A enrollment can apply retroactively up to six months once you file. One caller was working through exactly this trade when he called:
“would I be better off going to sign up for Medicare and going to the traditional plan and dumping the Health Savings Plan, or should I stick with the Health Savings Plan and postpone Medicare?”
There’s no universal answer to that. It depends on how much the account still matters to your plans and how close retirement actually is.
- 1Employer headcount20+ usually means you can delay without penalty
- 2Creditable coverage?Get HR’s confirmation in writing before deciding
- 3HSA still active?Any Part A enrollment stops future contributions
- 4Spouse or partner covered?Under-65 dependents need their own coverage plan
- 5Real retirement dateStart paperwork about 3 months before that date
- 6Health & family historyChanges how much waiting actually costs you
Where this usually lands
Most of these conversations settle into one of three paths.
Stay on the employer plan, delay Medicare. This fits people at a company with 20 or more employees, whose coverage is confirmed creditable, and who aren’t funding an HSA they still want to grow. The trade: you keep one bill and one set of rules now, and you enroll in Medicare later using a guaranteed window instead of the general one — with no penalty attached.
Enroll in Part A only, keep the employer plan as primary. Because Part A is usually zero-premium once you’ve worked enough, some people take it just to have it while the employer plan stays primary. This only works cleanly when there’s no HSA in the picture — otherwise it quietly shuts off contributions you may still be counting on.
Enroll in both Part A and Part B now. This fits people whose employer has fewer than 20 employees, whose coverage isn’t confirmed creditable, or whose employer plan has gotten thin or expensive compared to Medicare plus a Part D plan or a Supplement. The trade: a new monthly cost starts now, in exchange for certainty that nothing was missed.
None of these is automatically right. They’re right for different combinations of employer size, coverage quality, and what else is riding on the decision.
See where you land. If you would rather just talk it through with someone who does this every day, Most people can sort the direction quickly once the doctors, drugs, budget, and timing are on the table.
Why I lean the way I lean
When the facts check out — 20 or more employees, coverage confirmed creditable, no HSA in play — I lean toward delaying. The reasoning is simple: there’s no advantage to paying for coverage you don’t need yet, and the delay rules exist specifically to protect people who already have other coverage, not to punish them.
But I lean that way carefully, because the cost of being wrong isn’t small. If the coverage turns out not to be creditable and nobody checked, the Part B penalty is permanent — added to the premium for as long as you have Medicare, and it grows with roughly how many full years you went without coverage when you could have had it. That’s not a fee you pay once and move past. One caller asked the plain version of this fear:
“Am I going to be penalized if I don’t? How does that work?”
The honest answer is: probably not, if the employer is the right size and the coverage is confirmed. But “probably” is carrying a lot of weight in that sentence, and I’d rather spend fifteen minutes confirming it in writing than find out two years into retirement that the assumption was wrong.
When I’d tell you the opposite
I’d point someone toward enrolling now, even while still working, in several situations.
When the employer has fewer than 20 employees. Medicare becomes primary automatically at 65 in that case. Waiting doesn’t protect you — it just means claims may not get paid the way you expect, because the employer plan is assuming Medicare already paid its share.
When nobody at the company can actually confirm the coverage is creditable. If HR can’t answer clearly, or the plan documents don’t say, I’d rather get someone enrolled in Part B than leave it to chance. A penalty that follows you for the rest of your Medicare years isn’t worth saving a few months of premium now.
When the employer plan has gotten expensive or thin. Some employer coverage costs more every month than Medicare plus a Supplement or a Part D plan would, especially once a spouse is added to it. Staying on the employer plan at that point isn’t caution — it’s just an old habit costing real money.
When there’s no HSA left to protect. If contributions already stopped, or there was never an account, taking premium-free Part A costs nothing and starts the Medicare clock moving. There’s no reason to leave it sitting on the table.
Each of these flips the recommendation completely, which is exactly why I don’t answer this question in thirty seconds over the phone. Employer size and the state of an HSA change the whole shape of the advice.
Which side of that line are you on?
That is exactly the question a short Medicare conversation settles. You get me, not a call center.
What surprises people
Two things catch people off guard almost every time.
The first is that none of this happens automatically. Deciding to delay Medicare doesn’t file itself, and neither does deciding to start it. When the time comes, someone has to actually start the process. One caller asked me the plain version of it:
“So can I go down there? Do I need to wait on this appointment? Or can I just physically show up at the Social Security office and let them know I’m wanting to apply for my A and B?”
The answer is yes — but the timing matters. Starting the application a few months ahead of the date you actually want coverage to begin is what makes the transition land cleanly instead of leaving a gap in between.
The second surprise is that the clock for delaying Medicare and the clock for buying a Supplement without health questions aren’t the same clock, and they don’t reset the same way. Once Medicare starts, a guaranteed window opens for a limited time — and missing it, or not understanding it opened at all, can mean answering health questions later just to change coverage types. One caller had already sensed this, describing it in her own words:
“is there something where you have to… If you do that right in retirement, then you can switch to a supplement if you decide later, but you can’t start with a supplement and go back”
The specifics shift depending on the situation, but the shape of it holds: the order you do things in, and the timing, matters more going in than most people expect.
Where to go from here
If you’re still working at 65 and trying to figure out whether Medicare needs to start now, later, or in pieces, the answer depends on your employer’s size, whether your coverage is actually creditable, and whether you’re still funding an HSA — not on a rule of thumb from a coworker or a line from a commercial.
I can usually tell you which path fits within one phone call, once I know those three things. Book a call or call (270) 721-5069, and we’ll work through it together before any deadline sneaks up on you.
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Questions people ask me about this
Do I have to take Medicare at 65 if I’m still working?
Not necessarily. If your employer has 20 or more employees and the coverage is confirmed creditable, you can generally delay Part A and Part B without penalty for as long as that coverage lasts. If your employer has fewer than 20 employees, Medicare usually becomes primary at 65 whether you enroll or not, so delaying can leave real gaps. The safest step is getting written confirmation from HR before deciding either way.
What does ‘creditable coverage’ actually mean?
It means your employer plan is considered at least as good as Medicare’s standard benefits, which is what allows you to delay Part B later without a late penalty. It’s not the same as coverage simply feeling good — you need HR or your benefits administrator to confirm it specifically. Without that confirmation in writing, you’re guessing with a permanent penalty on the other side.
Will I be penalized if I don’t sign up for Medicare at 65?
If your employer coverage is confirmed creditable and you have 20 or more coworkers, no — you can enroll later using a guaranteed window with no penalty attached. If it turns out the coverage wasn’t creditable, the Part B penalty is permanent and grows with roughly how many years you went without it. That’s why confirming the coverage status matters more than guessing based on how the plan feels.
Can I keep contributing to my Health Savings Account if I take Medicare?
No. Once you enroll in any part of Medicare, including premium-free Part A, you can no longer contribute to a Health Savings Account. Because Part A enrollment can apply retroactively up to six months, this sometimes catches people who file for Medicare without realizing earlier contributions created a conflict. If an HSA still matters to your plans, it’s worth working through before you file anything.
What happens to my spouse’s coverage if I go on Medicare?
Your Medicare doesn’t extend to a spouse or domestic partner who isn’t yet 65 — they’ll need coverage of their own, whether through their own employer, a marketplace plan, or continuing on your former employer’s plan if that’s allowed. It’s worth pricing that out before you drop anything, since the cost of separate coverage can end up being a bigger factor than the Medicare decision itself.
When should I start the paperwork if I’m planning to retire soon?
A good rule of thumb is to start the Part A and Part B application about three months before you want coverage to begin, so there’s no gap between employer coverage ending and Medicare starting. If you’re also planning to add a Supplement, the guaranteed-issue window for that opens once Part B starts, so the timing of both matters together.
Keep reading
Start with the basics
- Medicare Questions Answered
- How to enroll in Medicare, step by step
- Medicare 101: the whole picture
- 64+ : the free book
More questions I get asked
- When to sign up for Medicare if still working (and you have employer coverage)
- Does Medicare Cover Dental, Vision, and Hearing? Where People Get Tripped Up
- Do You Need Hospital Indemnity With Medicare? The Gap It Is Really Solving
- Can You Be Denied a Medicare Supplement? The Timing Matters More Than People Think
- When should you sign up for Medicare and Medicaid (and what “dual” changes)
- Does Medicare pay for durable medical equipment when you’ve got a chronic condition?
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Written by Michael Smith, licensed insurance broker and founder of Guardian Health & Wealth in Bowling Green, Kentucky. I help people across the country make sense of Medicare : and I will tell you when the popular answer is not your answer.
Drawn from real conversations over the years. I never share anyone’s personal information : just the thinking, so you can see how a decision like this gets made.