Turning 65 used to come with a gold watch and maybe a slice of cake. Now it also comes with a new hobby:
decoding health insurance acronyms like you’re trying to crack a spy cipher. The big question a lot of people ask is,
“Can I get Medicare if I’m still working?” The short answer: yes. The better answer:
yesbut the smartest way to do it depends on your job-based coverage, your employer’s size, and your goals.
This guide breaks down how Medicare works when you’re employed, when you can delay parts of Medicare without penalties,
and the real pros and cons of signing up while you still have an employer plan. We’ll keep it practical, specific,
and (as much as possible when discussing insurance) human.
Quick Basics: What “Getting Medicare” Actually Means
“Medicare” isn’t one single plan. It’s a set of coverage parts you can mix and match:
- Part A (Hospital Insurance): inpatient hospital care, skilled nursing facility (limited), hospice, some home health.
- Part B (Medical Insurance): doctor visits, outpatient care, labs, imaging, preventive services, durable medical equipment.
- Part D (Prescription drug coverage): drug plans offered by private insurers.
- Part C (Medicare Advantage): private “bundled” alternatives to Original Medicare, often including Part D and extra benefits.
If you’re still working at 65, you can:
enroll in Parts A and B, enroll in Part A only, delay Part B, add Part D now or later, or choose Medicare Advantage
(depending on timing and eligibility). The trick is doing it in a way that avoids surprise costs and late enrollment penalties.
The Rule That Changes Everything: Who Pays First?
When you have Medicare and employer coverage, one plan pays first (primary), and the other may pay second (secondary).
The “who pays first” question is not triviait affects what you owe and whether you can safely delay Medicare.
If Your Employer Has 20+ Employees
In many cases, a group health plan from current employment at an employer with 20 or more employees
pays first, and Medicare can pay second. This often means you can keep your job-based coverage as your main plan and
delay Part B without a penalty while you’re covered through current employment.
If Your Employer Has Fewer Than 20 Employees
If your employer has fewer than 20 employees, Medicare is often expected to pay first once you’re eligible.
That’s why people in small companies are frequently advised to enroll in both Part A and Part B when first eligible.
If you don’t, your employer plan may not cover as much as you assumebecause it may “act like” Medicare should have paid first.
Translation: you could get stuck holding the bill.
Bottom line: Employer size matters. If you only remember one thing from this article, make it this:
your decision to enroll (or delay) should start with your employer’s headcount and how your plan coordinates with Medicare.
Can You Delay Medicare If You’re Still Working?
Often, yesespecially for Part B. If you (or your spouse) have group coverage through current employment,
you may be able to wait to sign up for Part B and avoid the late enrollment penalty. But you must do it the right way.
The Enrollment Windows You Need to Know (Without Needing a Decoder Ring)
-
Initial Enrollment Period (IEP): a 7-month window around your 65th birthday month
(3 months before, your birthday month, 3 months after). -
Special Enrollment Period (SEP) for Part B (working coverage): generally an 8-month window
that starts when your employment ends or your job-based coverage ends (whichever happens first). -
Part D timing with creditable coverage: if you delay Part D because you have employer drug coverage that’s
“creditable,” you typically want to enroll in Part D within 63 days of losing that creditable drug coverage to avoid a penalty.
One important gotcha: COBRA is not the same as “current employment” coverage.
If you leave your job and choose COBRA, that does not automatically extend the window to sign up for Part B without penalties.
So you can’t treat COBRA like a magic “pause button” for Medicare decisions.
Pros of Getting Medicare While Still Working
1) Extra Coverage Can Lower Your Out-of-Pocket Costs
If your employer plan is primary (common with 20+ employees), Medicare can sometimes serve as secondary coverage.
That can reduce what you pay for deductibles, coinsurance, or services where your employer plan is stingy.
Think of it like having a backup singer who occasionally steals the showin a good way.
2) Part A May Be Premium-Free and Useful as “Hospital Backup”
Many people qualify for premium-free Part A. If you don’t have an HSA issue (we’ll get to that), signing up for Part A
can add a layer of protection for inpatient hospital costs while you keep your employer plan for everything else.
3) You Can Protect Yourself From Late Enrollment Penalties
The Part B late enrollment penalty can stick around for as long as you have Part B. Avoiding it is worth real money.
If you’re eligible to delay Part B (because you have qualifying job-based coverage), you can waitbut you need to document
that coverage and enroll during your SEP when you stop working or lose employer coverage.
4) More Choice and Flexibility in Healthcare Planning
For some workersespecially those with frequent specialist visitsadding Medicare can broaden access and reduce surprise costs.
It can also simplify transition planning if retirement is near and you want to stagger changes rather than flipping everything at once.
Cons of Getting Medicare While Still Working
1) You Might Pay for Coverage You Don’t Need
Part B has a monthly premium, and if your employer plan already covers outpatient care well, you could be paying extra
for overlapping benefits. If your employer coverage is primary and robust, enrolling in Part B immediately may not be cost-effective.
2) HSA Contributions and Medicare Don’t Play Nice Together
If you (or your employer) are contributing to a Health Savings Account, here’s the headline:
Once you’re enrolled in any part of Medicare, you generally can’t contribute to an HSA.
That includes Part Aeven if it’s premium-free.
There’s also a sneaky twist: if you enroll in premium-free Part A after you’re already past 65, Part A coverage can be
retroactive up to 6 months (but not earlier than the month you turned 65). That retroactive coverage can turn
HSA contributions you made during that period into “excess contributions,” which can trigger tax headaches.
This is why people often stop HSA contributions months before enrolling in Medicare.
3) Coordination Confusion Can Create Billing Problems
When two plans are involved, billing can get messy if providers don’t know who pays first.
Some people experience claim delays, incorrect denials, or long phone calls featuring hold music that never deserved a Grammy.
If you enroll in Medicare while working, you’ll want to be proactive: tell providers you have both coverages and confirm the payer order.
4) Small-Employer Coverage Can Be Risky Without Medicare
If you work for a small employer and delay Medicare, the biggest “con” is not theoreticalit’s financial.
If Medicare should have been primary and you didn’t enroll, your job-based plan may not pay what you expect.
That can lead to large out-of-pocket costs that could have been avoided by timely enrollment in Parts A and B.
Part A Only While Working: Smart Move or Hidden Trap?
For workers at large employers, enrolling in Part A only can feel like a clever hack:
“Hospital coverage backup, no premium, I’m a genius.” Sometimes it is smart.
But it’s a trap if you’re contributing to an HSA. HSA eligibility generally requires that you not have other disqualifying coverage,
and Medicare enrollment is disqualifying for HSA contributions. If your financial strategy relies on maxing out an HSA,
delaying Medicare (including Part A) may be the better move until you’re ready to stop contributions.
Practical tip: If you’re in an HDHP with an HSA and love it, talk to HR and a qualified tax professional before you enroll in Medicare.
The cost of a mistake can be bigger than the cost of a few premiums.
Should You Enroll in Part B While Working?
Part B is where most working-at-65 decisions get interesting. Consider enrolling in Part B while working if:
- Your employer has fewer than 20 employees (Medicare often needs to be primary).
- Your employer plan has high cost-sharing and you expect lots of outpatient care.
- You want more provider choice and your employer plan is narrow-network.
- You’re retiring soon and want a smooth transition (and you’ve handled any HSA contribution timing).
Consider delaying Part B if:
- You have strong group coverage from current employment at a 20+ employee employer.
- You’re still contributing to an HSA and want to keep doing so.
- You’d be paying Part B premiums for benefits you rarely use.
What About Part D If You’re Still Working?
Prescription coverage is often the quiet “gotcha” because it feels optionaluntil you discover the late enrollment penalty.
If your employer drug coverage is considered creditable coverage (meaning it’s expected to pay, on average, at least as much as standard Medicare drug coverage),
you can usually delay Part D without a penalty.
When you eventually retire or lose that drug coverage, the typical advice is to enroll in Part D promptlyoften within 63 days
so you don’t create a gap that triggers the Part D late enrollment penalty.
Real-world move: Ask your benefits administrator for your plan’s annual “creditable coverage” notice and keep it.
If there’s ever a dispute later, documentation is your friend.
3 Real-Life Scenarios (Because This Is Where It Gets Real)
Scenario A: Large Employer, No HSA, Wants Extra Protection
Denise turns 65 and works for a company with 500 employees. She’s not using an HSA.
Her employer plan is primary, but she has frequent specialist visits. Denise enrolls in Part A
(and optionally Part B if the math works), using Medicare as secondary coverage. She checks provider billing setup so claims
don’t bounce around like a bad email chain.
Scenario B: Large Employer, HDHP + HSA, Maxing Contributions
Marco is 66, still working, and his retirement plan is “HSA first, questions later.”
He delays Medicare enrollment so he can keep contributing to his HSA. A few months before retirement, he stops HSA contributions,
then enrolls during his Special Enrollment Period, timing it so he avoids retroactive coverage problems.
Scenario C: Small Employer, Great People, Risky Coverage Setup
Linda works for a small business with 12 employees. She assumes her employer coverage will handle everything.
But in many small-employer situations, Medicare is expected to be primary at 65.
Linda enrolls in Parts A and B during her Initial Enrollment Period so she doesn’t end up with unpaid claims.
She coordinates benefits and breathes easier.
How to Decide: A Simple Checklist That Works in the Real World
- Ask HR: Is our plan primary or secondary to Medicare at 65? How many employees does the company count?
- Confirm drug coverage: Is it creditable coverage for Part D? Save the notice.
- Check HSA status: Are you contributing (or is your employer)? If yes, plan Medicare timing carefully.
- Price it out: Compare your employer plan premium + out-of-pocket costs versus adding Part B or moving to Medicare later.
- Protect your enrollment rights: If delaying Part B, learn the SEP rules and keep proof of employer coverage.
- Plan your exit: If retirement is near, decide which month you want employer coverage to end and Medicare to begin.
Common Mistakes to Avoid
-
Assuming COBRA extends your Part B safe window.
COBRA can be useful, but it doesn’t automatically protect you from Part B penalties if you miss your SEP timing. -
Not enrolling in Part B when Medicare should be primary.
This comes up most often with employers under 20 employees. -
Forgetting the HSA rule.
Medicare enrollment generally ends HSA contribution eligibilityand retroactive Part A can complicate timing. -
Not keeping documentation.
Save creditable coverage notices and proof of employer coverage in case you need it later.
Conclusion: So, Can You Get Medicare If You’re Still Working?
Yesyou can get Medicare while still working, and for many people it’s a smart move. The best choice depends on:
employer size, whether your coverage is based on current employment, your HSA contributions, and how close you are to retirement.
Big employer (20+ employees)? You may be able to delay Part B without penalties and decide whether Part A (or Part B) adds value.
Small employer (<20)? You’ll often want Medicare Parts A and B when first eligible to avoid coverage gaps.
HSA contributor? Plan carefullyMedicare enrollment and HSA contributions don’t overlap smoothly.
If you do one thing after reading this: talk to your benefits administrator, confirm who pays first, and map your enrollment timing
before you make a move. Medicare rewards planningand punishes guessing.
Real-World Experiences: What People Commonly Run Into (500+ Words)
If you ask a group of older workers what Medicare was like while still employed, you’ll notice a theme: nobody says,
“Wow, that was delightfully intuitive.” What you’ll hear instead are stories about timing, paperwork, and the occasional
“Wait…who’s paying first?” moment.
One of the most common experiences is realizing that HR and payroll teams may not live in Medicare-land.
People often report that their HR contact is helpful but not always certain how Medicare coordination works.
That’s not incompetenceit’s just that Medicare rules are specialized. The best outcomes usually happen when someone asks
very specific questions (“Are we primary or secondary to Medicare at 65?” and “Is our drug coverage creditable for Part D?”)
instead of vague ones (“Do I need Medicare?”).
Another frequent experience is the billing lag when someone enrolls in Medicare Part A or Part B mid-year.
Even when the coverage is correct, it can take a few claim cycles for doctors’ offices to route bills properly.
People describe getting an Explanation of Benefits (EOB) that looks “wrong” at firstbecause the provider billed the wrong payer order.
A quick fix is often to call the provider’s billing department and confirm what they have on file. It’s not glamorous,
but it can prevent delayed claims and avoidable collection notices.
Workers who keep an HDHP with an HSA often share a specific kind of Medicare story: the “I did everything right…
and then found out about retroactive Part A.” Many don’t realize that enrolling in premium-free Part A after 65 may
trigger retroactive coverage up to six months. In practice, people describe pausing HSA contributions earlier than expected,
adjusting payroll deductions, and sometimes requesting corrected W-2 reporting or withdrawing excess contributions.
The shared lesson is simple: if an HSA is part of your strategy, Medicare timing is a tax decision as much as a health decision.
Spouse coverage creates its own set of real-life experiences. Some couples discover that one spouse’s Medicare decision
affects the other spouse’s employer plan choices, especially if the working spouse carries family coverage.
People often talk about doing a “two-person math problem”: keeping employer coverage because it’s affordable for the spouse,
while enrolling the Medicare-eligible spouse in Part A only or delaying Part B until retirement. In families where the employer plan is expensive,
the experience sometimes flipsMedicare becomes the cost-saving path, and the couple restructures coverage so the employer plan is no longer the centerpiece.
Then there’s the emotional side: many people describe feeling oddly relieved once the decision is made.
Medicare has a reputation for complexity, but when the timing is right, it can simplify retirement transitions.
People who planned ahead often say the best experience was the smoothest handoff: employer coverage ends on the last day of a month,
Medicare begins the first day of the next month, prescriptions are lined up, and there’s no “gap week” of crossing fingers.
The common thread in the best stories isn’t luckit’s planning, documentation, and asking the payer-order question early.
If you’re still working and approaching Medicare eligibility, it may help to think of this as a mini-project:
gather plan details, confirm the rules that apply to your employer size, map your dates, and keep your paperwork.
You’ll still have to deal with a few acronyms, but you won’t have to deal with preventable penalties and surprise bills.
