Do I need to sign up for Medicare at 65 if I’m still working?

If you're still working at 65, and have group coverage, you don't have to enroll in Medicare right away.

Q: Do I need to sign up for Medicare at 65 if I’m still working?

A: Medicare eligibility begins at age 65, and signing up on time can help you avoid premium surcharges. But if you’re working at 65, you get a bit more leeway.

Medicare eligibility starts at age 65. Your initial window to enroll is the seven-month period that begins three months before the month of your 65th birthday and ends three months after it. Seniors are generally advised to sign up on time to avoid penalties that could prove quite costly over the course of retirement.

Specifically, if you fail to sign up for Medicare on time, you’ll risk a 10 percent surcharge on your Medicare Part B premiums for each year-long period you go without coverage upon being eligible. (Since Medicare Part A is usually free, a late enrollment penalty doesn’t apply for most people.) If you’re still working at age 65, however, a different set of rules applies.

No need to double up on coverage

Many seniors are no longer employed at age 65, and thus rush to sign up for Medicare as soon as they’re able. But if you’re still working at 65, and you have coverage under a group health plan through an employer with 20 employees or more, then you don’t have to enroll in Medicare right now. But if your employer has less than 20 employees, you need to take Medicare Parts A and B, because that will be your primary insurance. If you don’t enroll, your employer plan may pay less – or nothing at all – for your care when it finds out.

That said, it often pays to enroll in Medicare Part A on time even if you have health coverage already. It won’t cost you anything, and this way, Medicare can serve as your secondary insurance and potentially pick up the tab for anything your primary insurance (in this case, your work health plan) doesn’t cover.

The only exception is if you’re contributing to a health savings account and wish to continue doing so. Medicare enrollees are not allowed to contribute to an HSA, even if they continue to have coverage under an employer’s HSA-qualified high-deductible health plan.

Your Medicare special enrollment period

If your employer has at least 20 employees and you’re still working and covered under that plan when you turn 65, you can delay your enrollment in Medicare (specifically in Medicare Part B, which allows you to avoid the Part B premium while you’re covered under your employer’s plan). In that case, you’ll get an eight-month special enrollment period to sign up for Medicare if and when you leave your job or your employer stops offering coverage.  It will start the month after you separate from your employer, or the month after your group health coverage ends – whichever happens sooner.

Sign up during those eight months, and you won’t have to worry about premium surcharges for being late. And the eight-month special enrollment period is also available if you’re delaying Part B enrollment because you’re covered under your spouse’s employer-sponsored plan, assuming their employer has at least 20 employees.

But note that in either case, it has to be a current employer. If you’re covered under COBRA or a retiree plan, you won’t avoid the Part B late enrollment penalty when you eventually enroll, and you won’t have access to a special enrollment period to sign up for Part B — you’ll have to wait for the general enrollment period instead.

Run the numbers

Though you don’t need to enroll in Medicare at age 65 if you have coverage through a qualified group health plan, doing so might make sense if that plan isn’t heavily subsidized by your employer. Figure out what you’re paying for group health coverage and what your benefits look like under that plan, and then compare it to what you’ll pay under Medicare, taking into account the cost of everything from premiums to coinsurance to deductibles to copays.

Keep in mind that for comprehensive coverage under Medicare, you’ll need a Part D drug plan to accompany Parts A and B. Still, you might find that signing up for Medicare at 65 makes the most sense financially, even if you’re entitled to a special enrollment period later on.

Maurie Backman has been writing professionally for well over a decade, and her coverage area runs the gamut from healthcare to personal finance to career advice. Much of her writing these days revolves around retirement and its various components and challenges, including healthcare, Medicare, Social Security, and money management.

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David McCall

What if I’m turning 65, not retiring, working full-time, my employer pays 100% of my insurance premiums, our coverage is EXCELLENT… HOWEVER, we have LESS THAN 20 employees. Can I still defer signing up for Medicare or can I sign up, but refuse benefits until such time that I do retire in the future. (I’m paranoid, because our coverage is so good, I don’t want to risk any kind coordination of benefits between my primary plan and the Medicare plan to mess up or confuse my current coverage.) Thank you!

Maurie Backman

The 20 employees is, unfortunately, a requirement, which means you won’t qualify for a special enrollment period if you delay Medicare. However, if you want to keep your current health plan and sign up for Medicare, it could act as a secondary payer — meaning, it could pick up the tab for costs your primary insurance doesn’t cover. You’re allowed to have Medicare in conjunction with other insurance.


you need to sign up for medicare because your health ins will say they are secondary regardless if you sign up medicare or not and would be at risk of being stuck with high medical bills if you to be hospitaluzed

Josh Schultz

Hi David, to clarify this post — there is no number of employees requirement to access the special enrollment period, but your employer plan doesn’t have to pay as a primary insurer if there are fewer than 20 employees. This is why you’ll want to enroll in Part B in many cases, but it never hurts to check with H.R. / the insurer in the off chance you aren’t required to sign up. (Try to get a commitment to their policy regarding this so-called “coordination of benefits” with Medicare in writing.)

Judy Schroeck

Can that be 13 full time employees plus 11 part time employees?

Maurie Backman

Yes, as long as the plan is available to all employees to get to that 20.

Rosemary Robinson

Join the discussion…I and a number of other employees 65 and older are enrolled in an employer group medical plan and our employee count (full and part-time) has fallen below 20 employees in this 2020 year. My understanding is those employees 65 and older should now enroll in Medicare Part B because the private insurance carrier for those employees become secondary and Medicare will become primary. This is my question : What is the time frame in which the 65 and older employees must enroll in Medicare Part B in order to avoid a late enrollment penalty?

Maurie Backman

You should have eight months to enroll without penalty. Once your group coverage ends, you get eight months as part of a special enrollment period.

Maurie Backman

You have eight months to enroll without penalty. Once your group health coverage ends, you get a special enrollment period that lasts eight months.

Darlis G Smith

I will turn 65 on March 7, 2020 and I currently have health insurance for myself and my unemployed wife, and I an enrolled in an HSA which I contribute $1500 per year with a company deposit of $1000 per year, how does that affect me signing up for medicare part A.

Maurie Backman

You can no longer contribute to an HSA once you’re on Medicare. In fact, it’s advisable to stop HSA contributions up to six months prior to enrolling in Medicare, because you get up to six months of retroactive coverage through Part A. If you don’t stop HSA contributions, you could face a tax penalty.


I will turn 65 in March 2020. I am working and will not retire for 2 more years. It is my understanding that I should apply for Medicare Part A but continue medical insurance coverage under my current employer. I had to elect my HSA contribution several months ago. My full retirement age is 66 years 2 months. Does this influence the date when I should discontinue HSA contributions and apply for Medicare? Also, my employer contributes to my HSA to help offset the High Deductible plan we are enrolled in, will this need to be discontinued as well?

Maurie Backman

If you wish to continue getting health coverage through your employer and participating in your HSA, you do not have to sign up for Medicare at 65. You’ll get a special enrollment period that will allow you to sign up later without facing Part B penalties. If you need Part A for the backup hospital coverage, you can sign up for Part A alone, but that will mean losing the option to participate in your HSA. It sounds like you have good reason to keep that HSA, since you get employer contributions. But you’re also on a high-deductible health plan,… Read more »

What would be the purpose/benefit of retroactive coverage? I am having some difficulty making sense of that.

Debra Norris

when you say “employer has at least 20 employees” – does that mean 20 full-time, part-time or a combo? do all 20 have to be covered by the group plan?

Maurie Backman

It doesn’t matter if your employer has 20 full-time or part-time employees; the threshold is 20 to be considered a group health plan for Medicare special enrollment purposes.

You can qualify for special enrollment if the plan has fewer than 20 employees; Medicare will be primary vs. secondary to the group health plan based on the number of employees, though.

Karen Leyva

I’m confused on this, as, up to this point , everything was saying that you won’t be able to qualify for a SEP if you are over 65 and leave your employer coverage if the plan has less than 20 employees? can you clarify please?

Karen Leyva

Josh can you please clarify this regarding a SEP?

Hi Karen,

The number of employees doesn’t affect whether you qualify for a SEP. It does, however, impact whether your group health plan will pay before or after Medicare pays (meaning the number of employees your company will affect whether you choose to take Part B). This article has more info about Part B special enrollment:

jo ellen smith

I will still working when I turn 65 and I work for a public school and will continue to work until i am 67. Do I have to carry my school insurance if medicare is less costly when I turn 65

Maurie Backman

Once you’re eligible for Medicare, you’re allowed to sign up. Medicare won’t reject your enrollment if you have another health plan. But in your case, if you keep your insurance through your job, Medicare will likely serve as your secondary insurance, and your employer’s insurance will be primary. Generally, you’re not forced to keep health insurance through a job if you don’t want it. And Medicare will certainly not require you to keep it once you sign up.

Thomas Snyder

What about my wife if she is covered on my employer’s plan?

Maurie Backman

That counts for a special enrollment period. Your wife can enroll in Medicare later on without penalty if she’s covered by your group health plan and your company employs at least 20 people.


Is the 6 month retroactive period for medicare from the day medicare coverage starts or the day you apply for medicare coverage. EX. I want medicare coverage to start nov 1. I apply Oct 1. Do I have to stop HSA contributions on April 1 (6 months back from date I apply) or May 1 (6 months back from date coverage starts.

Maurie Backman

The six months of retroactive coverage applies when you sign up for Medicare after age 65. At that point, when you enroll, your coverage dates back to either six months, or your 65th birthday — whichever is shorter.

Josh Schultz

We recommend you speak with a tax professional for specific tax advice, but generally the rule is when coverage starts.

Dianne Levisohn

I am covered through my husband’s plan (he is over 65) And, he did not sign up for Medicare part A; We are both still working (full time). And, we are continuing to contribute to our HSA account through his office (>20 employees). I just turned 65, myself and am still planning on working for 3 more years ( starting part time in an office with <20 employees). Here is my question: 1. When he retires, presumably at the end of 2020, will I have a problem signing up for Medicare part A at that time? 2. Am I required… Read more »

Maurie Backman

1. You can sign up for Medicare Part A at any time now because you’re already 65; your husband’s retirement won’t impact your option there. 2. If you no longer have group health coverage, then you must sign up for Medicare Part B or otherwise face lifelong penalties on your premiums. 3. Since your husband is over 65, he should stop HSA contributions six months prior to retirement, since he will likely get six months of retroactive Medicare coverage. 4. It depends on how many people your company employs. If it’s less than 20 people then Medicare would generally be… Read more »

Eugene Siefker

I will be 65 in May 2020. At this time I work for an employer that has over 100 employees. I have insurance through my employer with a HSA account attached. I plan to work yet for a couple more years at least if health stays good. My wife is 3 months behind me in turning 65. She is also covered under my employers insurance as she does not work. Do I need to sign up for Medicare plan A and Plan B before turning 65 so as to avoid having to pay extra for the coverage later on because… Read more »

Maurie Backman

No, you don’t have to sign up for Medicare at (or right before) 65 if you’re covered by a group health plan by a company employing 20 people or more. You’ll get a special enrollment period for Medicare once you leave your job or once your group health coverage is taken away — whichever happens first. You won’t face Medicare penalties if you sign up during that period, which should be eight months long.

Nanette Greer

Do you still need to stop your HSA contributions 6 months prior to leaving your job/group health coverage taken away?

Stephen Marks

Thank you for a super helpful discussion, especially on the finer points of HSAs and Medicare!

Marion c.

Have been penalized for 15 yrs. Received Soc. Sec. at 65, but was not told to join Medicare. I retired at 70, had no insurance, was covered under my husbands plan as a NYC firefighter. Have complained over the years about the penalty, but to no avail. What can one do?

This sounds like a tricky situation. I’m sorry you find yourself in it. If somebody from the government (Medicare, Social Security, etc.) advised you not to take Part B when first eligible, you may qualify for “Equitable Relief” from your penalty. You can request relief if you have proof you were mislead by the government. You’d ask for help by writing a letter to Social Security with details of your specific situation.

Rich Carroll

Im 65 next week still employed with coverage- can I sign up A & B and delay until I stop working next year?

You are free to take Part A and B, Part A only, or defer taking Medicare at all. This article details some of the points to consider when making that decision — including the size of your employer.


Thank you so much for the above article. It is exactly what I need to read. It answered 95% of my questions.

Maurie Backman

So glad this was helpful!


I pay for my own healthcare. Can I sign up for Medicare at 65 and still work and cancel my our of pocket health care?

Maurie Backman

Yes, you can enroll in Medicare at 65 and stop paying premiums for your current insurance. You’re eligible for Medicare even if you continue to work.


I turn 65 in March, 2020, am employed by a large company, and my husband is on my company’s health insurance (& he is 7 years younger than I am). I contribute to an HSA account. If I intend to keep working, do I have to alert Medicare by registering on their website, or do I take no action with Medicare until I am ready to retire? I also have a question about my contributions to my HSA account. Do I stop contributing about 6 months before I intend to retire? What if I decide to retire suddenly and have… Read more »

Maurie Backman

You don’t have to tell Medicare about your work plans. If you don’t want to sign up for Part A (or B) when you turn 65, you can continue contributing to your HSA. Medicare will not force you to sign up at 65, and you’ll get a special enrollment period to sign up later as long as you have a group health plan and work for an employer with 20 or more people. It’s generally advisable to stop HSA contributions six months prior to signing up for Medicare if you’re enrolling after age 65 because retroactive coverage is automatic in… Read more »

Jitka Tybitancl

I have HSA and my company contributes $700 to it. I don’t contribute anything, I’m single. If I wanted to apply for Part A while I’m working, does the company have to stop contributing to my HSA?

Jim Hardee

If you are not signing up for Medicare at 65 and currently have company provided group coverage, are you required to verify this with Medicare? What I am trying to clarify is what exactly do you need to do to avoid these penalties for not signing up you refer to. How do they verify whether you have or didn’t have a group health plan? Thanks.

Nanette Greer

Your comments have been MOST helpful. I wish more of the seminars that I have attended would have addressed these situations and were less concerned with “selling” services. Thank you! Thank you!

melody Pedersen

I turn 65 in February. I plan on working for a few more year. Currently I pay about $140 a month for health insurance. I have read about the different Medicare plans and if I continue to use my work place insurance until I retire, will I be penalized? Do I need to sign a waiver before I turn 65 so I am not penalized when I eventually switch to Medicare?

Maurie Backman

If you have access to a group health plan through work and your company employs 20 people or more, you will not be penalized if you don’t enroll in Medicare on time. You’ll get a special enrollment period to sign up that begins once you either leave your employer, or once your group health coverage goes away.

melody Pedersen

Oh and I forgot to mention that my work place insurance does have HSA.

Maurie Backman

You can continue contributing to your HSA as long as you’re not on Medicare. It’s advisable to stop contributions six months prior to retiring/signing up for Medicare because if you enroll well after age 65 (which it sounds like you’re planning to do), you do get six months of retroactive Medicare coverage.

Audi Ritz

I will be 65 next month, I will continue to work for another year, I have employer medical coverage, they have over 20 employees. I also have an HSA and I will be making contributions throughout the year, 2020. So, if I understand correctly, I don’t have to sign up for Medicare this year while working. In addition, I should discontinue making HSA contributions 6 months prior to signing up for Medicare? Do I need to sign a waiver for Medicare at this time? Or provide documentation for having credible coverage? Thank you! AMR

Maurie Backman

You don’t have to sign up for Medicare this year if you don’t want to. If you’ll be enrolling in Medicare well after 65, you should half HSA contributions six months before you sign up to avoid tax penalties due to Medicare’s retroactive benefits rule.

D. Tenenbaum

Mr. Backman: Thank you for your website and the information in your article and responses. I’ve been looking for additional guidance since I first spoke to an SSA representative regarding my SS benefits. I received good information from the SSA office regarding the greater than 20 employees rule. I also know that when you sign up for SS – you are automatically enrolled for Medicare. Consequently, I am trying to make a decision on when to enroll for SS because of the impact of Medicare. I will turn 66 in April. My wife has health insurance coverage for us is… Read more »

Maurie Backman

If you have group health coverage through an employer with 20 or more people, that insurance is your primary and Medicare is your secondary. I can’t tell you when to sign up for Social Security, but I can tell you there are benefits to waiting. You can delay benefits all the way until age 70 and keep boosting them in the process.

D. Tenenbaum

So, I decided to sign up for Social Security at FRA (which is age 66 for me) and I got Medicare Part A retroactively for six months prior to my FRA. The nice thing about that was I had two hospital visits during the 6 months prior to signing up for Social Security. Those hospital visits were not entirely covered by my existing insurance. I am now waiting to see what, if any of the outstanding bills, will be covered by Medicare Part A. Thank you for your help Mr. Backman.

Diane F.

My husband will turn 65 before me. He works part time, has insurance from his previous employer of 35 yrs and we both have coverage on this plan. I also work part time, have full benefits from my employer and my husbands insurance is my secondary. My question is, 1- will Medicare effect my husbands current insurance plan? Will M’Care be his secondary plan, and can he hold off on part B? And he has a health savings plan with his insurance as well. This is all very confusing.

Maurie Backman

If your husband has a group health plan and works for a company of 20 people or more, he does not have to sign up for Medicare at 65. If he takes Part A only, which is free, Medicare will be his secondary. He can hold off on Part B and avoid penalties because of his group health coverage. If he wants to continue contributing to an HSA, then he will need to hold off on Part A as well. You can’t fund an HSA while on Medicare at all.

Scott Kuball

So, if I’m still covered through my employer when I turn 65 and decide to enroll in Medicare, I will be charged a premium?

Whether you also have coverage through your employer has no bearing on whether you’ll pay a premium for Medicare.

suzanne thorson

I will be eligible for Medicare in 3 months, work full time and have insurance through my company (20+) which is just ok. There is a steep inpat per day copay though so I think I will sign up for Medicare Part A. I contribute to a FSA, not a HSA. That is still okay though, right?

You are correct that unlike with a Health Savings Account (HSA), having Medicare Part A does not disqualify you from contributing to a Flexible Spending Account.

If you’re currently working full-time and she is covered through your plan, she may be able to safely delay enrolling in Medicare.

Marie Sutton

My husband is turning 65 on 3/15/20. He has Medicare A for 11 years because he is permanently disabled. he is covered under my employer’s health plan and will continue to be for at least 2 years. Thus we are not going to sign up for Part B until his coverage under my employer ends . Do we have to notify Social Security or someone else that he will not be enrolling because he has coverage under me or do we just do nothing ?

Maurie Backman

You should be able to do nothing and not enroll in Part B until you’re ready to. Medicare enrollment at 65 is not automatic – they don’t sign you up just because you reach 65.


can you request medicare to start the day you sign up or do you have to accept the 6 month retro back

Maurie Backman

The six months of retroactive benefits applies when you enroll in Medicare after 65. At that point it’s automatic and you can’t accept or reject it – it just happens. For example, if you enroll at 65 1/2, you’ll get Medicare dating back to 65.

Medicare Part A is retroactive up to six months; Part B and D are not.


I turn 65 this month but not retiring till I’m 67.5. I don’t participate in HSA and my employer has over 20 employees. If I enroll in Medicare part A, will I still be penalized for late enrollment foe part B?

Maurie Backman

You won’t be penalized on Part B penalties as long as you still have group health coverage through your job.

Phyllis Musick

What about if you are covered under your spouse’s insurance

Maurie Backman

If you’re covered under a spouse’s group health plan at a company with 20 or more employees, you do not need to sign up for Medicare at 65. This applies whether you are or aren’t working.

Maurie Backman

That counts as you having a group health plan for Medicare special enrollment purposes.


I am over 65 but still working with group medical insurance and HSA. Can Medicare Part A pay my group insurance deductible? Can I only enroll Medicare Part D ?

If you enroll in Medicare Part A, you’ll have to stop contributing to your HSA. And you can only enroll in Part D if you’re also enrolled in Part A and/or Part B. If you do enroll in Medicare, it will either be primary or secondary to your group coverage, depending on the size of your employer (if your employer has 20+ employees, it will pay first and Medicare will be secondary; if your employer has fewer than 20 employees, Medicare will be primary and your employer’s plan will be secondary). You’ll want to talk with your employer to see… Read more »


My question is about the 20 employee portion. I work in a small school district which has a insurance plan that is in a joint trust. This means that several school go together and are under 1 group. Our school is right under 20 employees but our group health insurance plan is well over the 20. Can I count the group health plan for my qualification to stay under my employers group health insurance. I receive insurance here with little out of pocket expense and I would have to pay more to go to Medicare. If I have to go… Read more »

Hi Denise,
You’ll need to check with the health plan administrator to find out for sure whether your plan provides secondary or primary coverage for employees with Medicare. As long as at least one of the other schools in your joint trust has at least 20 employees, the plan should provide primary coverage for everyone in it. But small employers can ask for an exception to that rule, so you’ll have to check with your specific plan to make sure. This slide from CMS might be helpful for you:


Turning 65 in April. Still and will continue working in a company of 13 employees. I understand I will have to enroll with Medicare Part A and B. So,when I get Medicare,my company insurance which pays 50 percent of my current insurance ,what are the options I have to avail from my company’s health plan? When my Medicare starts, and as am still working, will there still be deductions for Medicare on my salary?

Josh Schultz

Medicare wouldn’t be deducted from your payroll (other than the payroll taxes already deducted for Part A). Instead, you’ll receive a bill for Medicare Part B for as long as you aren’t yet collecting Social Security.

Maurie Backman

Your employer cannot charge you for Medicare; it can only charge you to continue participating in its health plan. If you don’t continue to participate, then you shouldn’t be charged. Once you have Medicare, you may not need the health plan your employer provides. You’ll need to review its coverage and determine if it’s worth the cost. Meanwhile, you will continue to pay Medicare taxes ( FICA taxes) on your income until you stop earning wages.

Mary Cunningham

I don’t have employer provided healthcare. I begin Medicare when I am 65,but I will continue to work full time with no employer benefits. Since I am not receiving SS do I have to pay a monthly part A premium?

Josh Schultz

You won’t have to pay a premium for Medicare Part A as long as you or your spouse have worked for 10 years where you paid Social Security taxes.

Maurie Backman

You only pay a Part A premium if you didn’t pay enough lifetime Medicare tax on your earnings. If you worked and paid Medicare taxes for 10 years or more, or have a spouse who did, then you won’t be charged a premium.

Jim L

I turn 65 in the next 4 months. I currently work for an employer with 20 employees. Some years there are 22 and some years less than 20. I’m gathering I should sign up for Part A (no cost) and defer Part B until a year in which there are less than 20 employees covered or I choose to exit employment. Am I thinking corretly?

Josh Schultz

In situations like this, it may help to get written confirmation from your HR benefits department and/or health insurer regarding whether the plan considers itself to be primary or secondary to Medicare. According to the Federal government, the 20-employee threshold is met and Medicare becomes secondary payer “if the employer employed 20 or more employees for each working day in each of 20 or more calendar weeks in the current or preceding year. Note that the 20 weeks do not have to be consecutive.” More information is available on page 8 here:

Josh Schultz

It might in some way make sense to keep Medicare Part B even if your plan switches back and forth between primary coverage, just to avoid uncertainty. That said, you should qualify for Special Enrollment into Part B if you do decide to delay enrollment.

Jim L

If your income is high though, the Part B premium is quite expensive.

Marcia T.

My spouse is 65, is employed with health care coverage in a workplace with >20 employees and has not yet enrolled in Medicare. He will retire in March 2020 with health care coverage continuing through May 31. We will be out of the country for April and May 2020 and want our Medicare (A and B) to be effective June 1 2020. I am covered under his health care coverage but have Medicare part A and will begin receiving my social security payment in March. He is electing to delay his SS benefit until 2021. I was given a form… Read more »

Josh Schultz

Hi Marcia, Both you and your husband should consider enrolling for Medicare Part B right when he retires. You are taking a risk delaying Part B because once he retires Medicare is his primary insurance, regardless of the number of employees at his firm and whether you’re actually enrolled. If you or he need medical care, the insurance may not pay because it could consider Medicare as his primary coverage. While you and he may have up to 8-months during which you can enroll in Part B when he retires, delaying enrollment is risky. That said, you can specify a… Read more »

Tracy St.Denis

My husband is eligible for medicare in March but is still working full time and will continue to do so until he is 70. I and our son are covered under his company insurance which includes an HSA. I won’t be 65 until 2025 and our son will be 26 about the same time. We plan to continue with the company insurance for those reasons. My question is that his company sent him a letter that he had to DECLINE medicare part A by responding to his Medicare communication and following the instructions provided. He hasn’t received any communications from… Read more »

Josh Schultz

It sounds like you’ve thought this through. You are correct, your husband doesn’t need to decline Part A. He won’t be enrolled in Part A unless he’s collecting Social Security benefits (and it sounds like he is not). Be sure to be mindful that when he does take Social Security, he will be enrolled in Part A, effective six months retroactively. Having Part A will disqualify any HSA contributions he makes for that portion of the year, which could lead to penalties.


I’m a little confused over this statement… “If you’re covered under COBRA or a retiree plan, you won’t avoid the Part B late enrollment penalty when you eventually enroll, and you won’t have access to a special enrollment period to sign up for Part B — you’ll have to wait for the general enrollment period instead. I am currently 64. I will turn 65 in July, 2020. I have excellent health insurance through my employer (> 20 employees). I contribute to my HSA. I will retire on May 1, 2021. 1. I guess I shouldn’t contribute to my HSA in… Read more »

Maurie Backman

1. When you sign up for Medicare after the age of 65, you’re given six months of retroactive benefits. If you’re retiring in May 2021 but turn 65 in mid-2020, I’d advise stopping HSA contributions six months prior to retirement, assuming you’ll get on Medicare as soon as you retire. 2. Only you are in the best position to decide when to actually retire. The point of this article is to walk you through some scenarios regarding Medicare enrollment. 3. Again, the decision to sign up for Parts A and B is up to you. Generally speaking, it’s a good… Read more »


Thank you for taking the time to respond.


I work part time, am covered under husbands insurance plan with union sheet metal,and turn 65 next month. I had to enroll in part A and B per the union . I am very healthy and want to know why i am paying for two insurance coverages

Maurie Backman

Unfortunately I’m not familiar with union laws mandating that you sign up for Medicare at a given time. I would suggest addressing that issue with a union representative and going from there. Some people choose to pay for health coverage through an employer plus Medicare. If you’re not being given a choice then that’s something to first address with the entity that’s forcing you to obtain Medicare.

Michael Redmond

I turn 65 this year and work for the federal government. Currently I have health insurance through my employer, plus Tricare as a secondary as I am also retired military. I plan on signing up for Medicare, but as I am still working, keep my health insurance through my employer. Once I retire, I plan to keep my health care through my employer, plus Medicare, plus Tricare for life. That should cover everything that could possibly happen (I think) and I assume either my health care plan through my employer or Tricare for life would be my part B, C… Read more »

Maurie Backman

It’s hard to say whether all of that coverage will pay for absolutely every medical service you’ll ever need. Plan rules and scope of coverage can change over time. But it certainly sounds like you’re covering all of your bases!


Is there a form that needs to be filled out by my employer stating that I have coverage through them?
I will turn 65 in June but plan on working until I am 67. I would like to sign up for Part A (no cost to me-correct?)

Most people qualify for Part A for free; you can sign up unless you’re contributing to an HSA, in which case it’s best to delay enrolling until you also take Part B. You’ll request the Part B enrollment form from Social Security when you’re ready to retire from your firm. This comes with an employer request for information form known as L564. Your employer can fill in that you’ve had coverage through them since the month you turned 65, thus qualifying you for special enrollment into Medicare Part B.

I have group coverage through my job. I am 66 years old I have Medicare part a & b and the job is closing April 31, 2020 and the job is offering us 6 months free medical coverage from end date. We also have retirement medical coverage and base on your age and years of service determine how much the company is going to pay and I think that this amount for me will be around 65 to 80%. I do not know what way I should be going and it seems like I am over paying now are when… Read more »

Maurie Backman

If you have group coverage already and are already signed up for Medicare, you might as well take that free coverage so it can serve as your secondary insurance. You’re also allowed to drop your Part B coverage and sign up again once you need it. But if you enrolled in Medicare despite having health coverage, it leads me to believe that your employer coverage left some gaps, which is why you chose Medicare. Either way, you have the option to stop Medicare and sign up again when you need it.


I am turning 65 in July 2020. I am still working and I have full benefits with my company and I want to continue that until I retire. DO I sign up for Part A now and wait on Part B ? Also, do I need to get something from my employer proving I am still working when I sign up for Part A?

Maurie Backman

You can sign up for Part A at 65 if you choose and use it as secondary insurance in case you need hospital care. When you enroll, you’ll be asked if you want to sign up for Parts A and B, or Part A only. You’ll then be asked to name your employer, confirm that you have health insurance through that employer, and indicate how long you’ve been working there. These are questions you answer directly via on online form.

Zina Puchalski

My husband is turning 65 here in April, hes not planning on retiring till late fall maybe? its still up in the air. He works for a city in a small town and ther are only two employees, but they are in a group medical plan with other towns. he is wondering if he has to sign up for medicare? he has worked for the town for over 20yrs. he has employer paid insurance.

Whether or not you can safely delay Part B depends on whether the employer-sponsored plan will be primary or secondary in conjunction with Medicare. If it’s primary, you can generally delay Part B, whereas if it’s secondary, you can’t. When very small employers join together with other employers in situations like this, the plan will provide primary coverage (with Medicare secondary) as long as at least one of the employers has 20+ employees. So it depends on how many employees the other towns have. But employers can also ask for exceptions to the primary/secondary rule in that circumstance, so he’ll… Read more »

Amalia Pose

I’ m retired and since 2016 in Medicare. Recently, I started a part-time job and saw that the company in withdrawal money for Medicare. Is this correct? I already pay my medicare from my social security.

Maurie Backman

What you may be seeing is Medicare taxes taken out of your earnings via payroll. That’s standard.

Micaela C Ayers

This is so helpful! I’ve found significant help reading the questions and answers. My question relates to my current HSA this year 2020, and the timing of contributions. I am 65, working at a large college, have HSA for 2020. I want to retire Feb. 1, 2021 for pensions purposes, and apply for Medicare coverage to start Feb. 1, but it looks like it will start instead March 1st. “It will start the month after you separate from your employer, or the month after your group health coverage ends – whichever happens sooner.” Which is right, the Feb. 1 or… Read more »

Maurie Backman

The “start the month after you separate from your employer” bit refers to your special enrollment period. You can sign up for Medicare so that you begin your coverage on Feb. 1 of 2021, at which point you’d want to cease HSA contributions in July of 2020. As long as you’re 65, Medicare will take your money and give you coverage — even if you’re still employed and covered by health insurance. So if you want your coverage to begin in Feb 2021, that’s your decision.

Micaela C. Ayers

‘cease in July’ … Does that allow me to make the July month contribution in this year? I figure Jan, Feb, Mar, Apr, May, Jun, July = 7/12 of 2020 contribution limit, since: Aug, Sep, Oct, Nov, Dec, Jan = 6 months Medicare backdating. Yes? No? Please help with this final detail.

Karen Nova

I turn 65 in March 2020. I am training someone to fill my position which will likely take until May or June. I signed up for an HSA and want to purchase glasses before I cancel my policy with the monies that I have contributed. Do I still sign up for Medicare in March without being penalized for my current HSA status. I plan on signing up for an Medicare advantage plan, and was planning on doing that just before i give them my notice. T

Hi Karen, when you enroll in Medicare Part A, you will be penalized for continuing to contribute to an HSA. Your Part A will take effect back to the date you qualified for Medicare (usually the month of your 65th birthday). So, you’ll want to plan your HSA contributions accordingly. You might have to contribute less for the year.

Paul Lumley

I will turn 65 on July 6, 2020 so I will start Medicare on July 1, 2020. I will retire from my large employer on June 30, 2020 and that will be the last day of my health coverage through my employer. Can I continue to make HSA contribution through June 2020, or do I need to stop 6 months before July 1, 2020. Thank you.

Maurie Backman

You should be okay to keep making HSA contributions through June 2020 because Medicare retroactive benefits can only date back to your 65th birthday. But it looks like you’ll be enrolling at Medicare at 65, in which case you don’t get retro benefits because you weren’t entitled to them prior to 65.

Paul Lumley

Thank you so much Maurie. This is also my understanding, however unfortunately the counselors at both Medicare and Social Security didn’t draw the distinction between retiring right at 65 and retiring later, and they both advised me to stop HSA contributions at age 64.5 which you and I agree is incorrect.

Cherie Miller

I have a question. I have private health insurance. I like it. I am a subcontractor for a co. But pay for and cover my own cost. I am turning 65 in may. Have tufts health commect i qualifyed for. I have dental also. Will i get a penality if i choose not to sighn up yet.?

If you are turning 65 and have employer-based coverage through your own job, you can delay signing up. Is the insurance through your work, or do you buy it separately/individually? If yes, then you should consider signing up for Medicare or you could face Part B enrollment penalties, denied claims, or more.

Russ Vogt

Just turned 65, working for company with +20 employees. Plan to continue working. If I take just Part A, then job gets downsized during my initial open enrollment period can I change my status and enroll in Part B and D?

You should qualify for special enrollment into Part B and/or D if you have employer-based coverage since the time you qualified for Medicare. Your coverage under Part B and/or D could begin as soon as the following month.


My husband will be turning 65 in the fall. His employer has approx. 500 employees however there are two medical plans, one for employees living in PA and one for the employees living out of state. The total number of employees living out of state is currently at 3 (ages are 65, 55, 34). Would he be required to sign up for medicare or can he continue to remain on the company medical plan?

Your husband’s work-based insurance would pay primary, or first, and Medicare will pay second (if he enrolls in it). As long as he’s still actively working, he does not need to take Medicare. Be sure to check with his work-based prescription drug plan to see if the coverage is “creditable” for Medicare Part D; this can help him avoid late enrollment penalties into that program once he does retire.

Debby Malcolm

I work full time for a company with thousands of employees. I am covered by their health care plan. I contributed to my HSA last year through June, planning to start Medicare in January, 2020. Medicare rolled it back to May, my birthday. I un-enrolled. Some of the people at the Social Security office had knowledge of that, and I have a letter. Medicare had no notice, nor did my local Social Security office. I was then ready to enroll, but was caught in the middle. Social Security told me that even if I enroll in Part A years from… Read more »

Dave Malcolm

Meant to add to my problem shown above — a Social Security employee told me that to avoid starting Medicare on my 65th birthday, regardless of when I apply, I would have had to make the request six months BEFORE my 65th birthday. Talk about confusion.

Maurie Backman

Based on the complexity of your situation, you may want to speak to a tax professional or attorney to help you sort through this matter. Unfortunately, people are given bad information from Social Security employees all the time. A legal professional may be able to advise you of your rights when this happens. Generally speaking, the most that can happen when you fund an HSA while being eligible for Medicare is that you’re assessed a tax penalty on the contributions you put in tax-free during that time.

Melanie Freeman

Thank you for the very helpful information. In my situation, I would fall into the special enrollment period since I am 67, and covered by my employer’s non- HSA health insurance plan with over 50 employees participating. I will drop down to 24 hours per week January 2021, and will no longer be eligible for this benefit. To enroll during this 8 month period, what proof of previous insurance will I need when I sign up for Medicare? Is there a specific government form that I need to submit? Thank you.

Maurie Backman

You can contact the Social Security Administration at 800-772-1213 for more information, but in a nutshell, you’ll ask for a couple of specific forms that you’ll fill out or have your employer fill out. These are Form CMS 40B and CMS L564. That’s how you’ll provide proof that you’re entitled to a special enrollment period.

Wippiam lowry

I turn 65 in 3 months and I am currently insured with the affordable health care act/Obama care.. What will happen to my Obama care at that point? It’s the best thing that ever happened to me I want to keep it as it is.

Louise Norris

This article will be useful for you: I can’t speak to your specific situation, but it’s unlikely that keeping your individual market plan is going to be a good idea. It won’t coordinate with Medicare, and if you’re getting premium subsidies in the exchange, those will terminate when you become eligible for Medicare, assuming you have enough work history (10 years) to qualify for premium-free Medicare Part A. And if you delay your enrollment in Medicare because you’re opting to keep an individual market plan, you’ll face late enrollment penalties for Part B and Part D if and when… Read more »