I’m retiring next year—do I need to do anything with my Medicare?

Question

Lea Ayres · Accepted Answer

If you're retiring next year and turning 65, you'll need to sign up for Medicare (Part A and Part B) through Social Security, either online or by contacting your local office, to avoid potential gaps in coverage or penalties.

Answered by Lea Ayres on March 12, 2025

Broker Licensed in PA, CT, MD & 8 other states

Answered by Lea Ayres Medicare Insurance Agent

Larry Dalton · Answer

I recommend starting your Medicare Part A & B, six to four months before your 65th birthday. The Medicare system is very slow and prepared for the unknown. Medicare supplement/Medigap or Medicare Advantage plans can be attained three months before your 65th birthday or retirement from a group insurance plan. You can often begin your supplement/Medigap plan before you receive your Part A and B Medicare numbers. All plans will go into effect gently on the first day of the month you turn 65.

Answered by Larry Dalton on March 26, 2025

Broker Licensed in OK & TX

Answered by Larry Dalton Medicare Insurance Agent

Brian Moore · Answer

Since you’re retiring next year, you’ll need to enroll in Medicare during your Initial Enrollment Period, which spans the three months before, the month of, and the three months after your 65th birthday—assuming you’re not already on it—but my advice is to start reviewing your options now rather than waiting until the last minute. Get familiar with Medicare Parts A, B, and possibly D or a Supplement plan, and jot down questions for a professional you trust, because diving into this complex process without preparation can leave you rushed and short on time to pick what fits your health and budget. I’ve seen too many folks scramble as retirement hits, so giving yourself a head start ensures you’re set up with confidence when the time comes.

Answered by Brian Moore on March 27, 2025

Broker Licensed in OH

Answered by Brian Moore Medicare Insurance Agent

Melonie Wood · Answer

Someone who is retiring and has Medicare Part A & is still on employer insurance will need to have their employer obtain the employee's Part B. Otherwise they will be unable to get any kind of Medicare Advantage OR Medicare Supplement

Answered by Melonie Wood on March 30, 2025

Agent Licensed in FL & AL

Answered by Melonie Wood Medicare Insurance Agent

William Lawler · Answer

If you are retiring and losing your health coverage through work, you need to make sure you enroll in Part B within 60 days so that you mat enroll in a Medicare Advantage or Medigap plan.

Christopher Boyd · Answer

You need to inquire about Long Term Care planning, as you cannot rely on Medicare funding or the Medicaid Spend Down provisions to be pleasant for you or your family. If you are eligible for credible healthcare coverage from your employer, you will most likely not need to inquire into Medicare enrollment until 90 days before you plan to lose group coverage and enroll into Medicare, assuming you are going to be 65 or older or are not under the SSDI provision of automatic Medicare enrollment.

Answered by Christopher Boyd on March 4, 2025

Agent Licensed in IN, KY, MI, OH, PA & TN

Answered by Christopher Boyd Medicare Insurance Agent

Robert Pennington · Answer

If you’re retiring at age 65, you can apply for Part and B three months prior to your birth month.  This allows time to to get this in place so you can research Medicare Plans.

Christopher Palazzini · Answer

Yes! You need to figure out if you are enrolling into Medicare during your initial enrollment period or will you wait until after and enroll during a SEP and submit additional paperwork to eliminate penalties.

Answered by Christopher Palazzini on March 25, 2025

Broker Licensed in FL, CA, GA & 6 other states

Answered by Christopher Palazzini Medicare Insurance Agent

Bill Green · Answer

Yes, if you're retiring next year and will be losing employer coverage, there are a few important Medicare steps to plan for. First, make sure you enroll in Medicare Part A (unless you have a HSA plan). Then when you are at least 3 months from retirement apply for Part B using the proper forms from social security (CMS40B and CMSL564) if your employer coverage is ending. You’ll want to time your enrollment so there’s no gap between your work coverage ending and Medicare starting. If you’ve delayed Part B because you were still working, you qualify for a Special Enrollment Period, which helps you avoid penalties and let's you pick any plan you want without health quetions. You’ll also need to decide whether to add a Medicare Advantage plan or a Supplement plan, and a Part D drug plan, depending on your health needs and budget. Talking with an experienced agent ahead of time can help you make a smooth transition and avoid any surprises.

Answered by Bill Green on March 26, 2025

Broker Licensed in FL, AL, AZ & 19 other states

Answered by Bill Green Medicare Insurance Agent

Amy Putrino · Answer

It's never too early to do your homework. Many individuals approaching Medicare fear that it will be too expensive or not cover them as well as their current coverage. Taking the time to fact find and gather information can put your fears to rest and help you feel comfortable with your future transition to Medicare. You can also discuss a timeline for applying for Medicare Part B and other requirements with your trusted Medicare plan advisor.

Answered by Amy Putrino on March 26, 2025

Agent Licensed in RI, CT, FL & 11 other states

Answered by Amy Putrino Medicare Insurance Agent

Karen Boudreaux · Answer

It depends on if you qualify for Medicare. And if you do and you were on your company’s insurance, you have to apply for part B if you are on your companies insurance, you have a special election. Even if you’re after the age of 65.

Answered by Karen Boudreaux on March 13, 2025

Agent Licensed in TX, AZ, CA & 5 other states

Answered by Karen Boudreaux Medicare Insurance Agent

Mark Maliwauki · Answer

You will have 63 days from your last coverage date to enroll in a qualified Medicare plan. This can be a Medicare Supplement or Medicare Advantage plan or Original Medicare with a drug plan.

Samantha Jellison · Answer

If you are already enrolled in Part A and Part B, and you have either a Medicare Supplement with a Prescription Drug Plan (Part D) or a Medicare Advantage with Prescription Drug Plan, there is nothing more to do than to enjoy your retirement!

If you are transitioning from an Employer group insurance plan or you delayed Part B past the age of 65, there will be some additional steps you will need to take. 
This is when it is best to talk to a licensed agent/broker, who can guide you on the next steps in order to make your transition to retirement that much more effortless.

John Stagner · Answer

Two possible scenarios - and the answer is yes for both. 

Scenario 1: You are retiring at age 65. If you do NOT take medicare at age 65, you will have a lifetime penalty when you do finally enroll. The penalty will be for Part B AND for Part D. If you are drawing Social Security already, your Medicare will start automatically. If you are NOT drawing Social Security, your will need to self-enroll. You do that at ssa.gov.

Scenario 2: You are retiring AFTER age 65. In order to avoid late enrollment penalties, two conditions had to exist since age 65: you worked for an employer with 20 or more employees AND you had insurance with that employer. If either of those stop (i.e. retirement), you must enroll into Medicare to avoid penalties. You will need two forms: CMS 40B and CMS L564. The 40B is your request to start Medicare. The L564 is filled out by your employer(s) verifying you were covered by their insurance since age 65. If you had multiple employers since age 65, you will need the L564 from each employer.

Lynn Mut · Answer

Timing with Medicare can be tricking.  It's always best to review with an agent to find out the ins and outs with Medicare.

There are different guidelines for people who are still working and already 65 vs just turning 65.  There is a lot to unpack with this question.

Setting an appointment with an agent to review with you is always and highly recommended.

Gregg Matheny · Answer

Yes, if you are currently over the age of 65 and you are on some type of employer coverage Then at least a month prior to your employer coverage canceling you’ll need to Get a hold of Social Security (I like SSA.Gov) and apply for Medicare part B only. You will subsequently get a few letters from Social Security stating that they need information about your previous employer plan before they start Part B. You may even need paperwork signed from your work so it’s best to give SSA plenty of time to start Part B.

Answered by Gregg Matheny on March 25, 2025

Agent Licensed in AZ & UT

Answered by Gregg Matheny Medicare Insurance Agent

Leslie Helene Sussman · Answer

Yes if you are 65 and / or Medicare eligible please contact a Medicare broker to review options.

Steven Bleicher · Answer

If you've been happy with the coverage since you turned age 65 and applied for Medicare, then most likely the ONLY aspect of healthcare to review each year surrounds the Rx's that have been newly prescribed OR those which are Brand Name drugs (Tiers 3, 4 and 5) for which the global economy has adversely affected its cost from one year to the next. Please remember that a Part D(rug) plan may be your best choice in one year but not necessarily as good for you in the subsequent years. NOTE: Please read your "ANOC" or the Annual Notice of Change which is mailed to your home every late October/early November. Steve

Answered by Steven Bleicher on March 25, 2025

Broker Licensed in AZ

Answered by Steven Bleicher Medicare Insurance Agent

Tasha Riggs · Answer

You need to get a Medicare advantage or a Medicare supplemental. You don't want just Medicare. You would be responsible for 20% for all bills with no end in site.

Michael Kim · Answer

Yes. You would need to call Social Security to schedule a call to sign up for your SS benefits along with your Medicare Part A and Part B.

Julie Joyce · Answer

Good  time for a review!  Every year the plans change and your needs and life will probably change once you retire.

Helena Foutz, RSSA · Answer

It depends! How old are you? If you're a younger retiree and will still get health coverage from your employer, stay on that coverage. However, if you have already passed your Medicare Birthday (age 65) and didn't do anything, then you need to get going and apply for Medicare Part A and B. Some people apply for just Part A when they turn 65, so for those with Part A, they just need to apply for Part B and select a plan!

Answered by Helena Foutz, RSSA on March 4, 2025

Broker Licensed in CA, AK, AR & 12 other states

Answered by Helena Foutz, RSSA Medicare Insurance Agent

Shelly Hefley · Answer

YES - you need to talk to a financial planner like myself to be sure your insurance is compliant and to determine if you need part B or not.

Ryan Raphael · Answer

If you are retiring next year and are apart of 20 or more employees, you do not need to do anything with Medicare until you are within 3 months of your retirement date.

Aaron Solomon · Answer

It is important to make to sign up immediately for Part A. Part A is free. If you fail to sign up for
Part A, there is a penalty. You have 90 days from your birthday.  If you are retiring , you can sign up for both Part A and Part B.

Joseph Peck · Answer

Its best to look into it early so they know what to expect and when so there is a game plan. Want to start early due to the fact that we are dealing with the government and if there is something else needed we can get it taken care of with no last minute surprises.

Answered by Joseph Peck on March 26, 2025

Agent Licensed in MI, AL, KS & TN

Answered by Joseph Peck Medicare Insurance Agent

Peter Yeh · Answer

Whether you’re turning 65, are already 65, or are older than 65 it doesn’t matter. If you’re planning to retire in 2025, these are some key things you should consider.

Talk with your employer benefits administrator early – at least 6 months before retiring if possible.
Ask how your spouse/dependents may be impacted when you drop your employer coverage. They could be eligible for COBRA.
Ask if you have retiree coverage available, how it may work with Medicare and if it’s available to your spouse/dependents.
If you are over 65, and you were able to delay enrolling because you had creditable health coverage, make sure before you enroll to get written proof of your prescription drug coverage to avoid late enrollment penalties for Part D. Your employer provides this. 
Identify and mark your calendars for your Initial Enrollment Period dates (if you’re under 65 or will be 65 at retirement) or for your Special Enrollment Period dates (if you’re over 65 and qualified to delay enrollment). 
Enroll as soon as you can. Whether it’s the first month of your Initial Enrollment Period or Special Enrollment Period, enroll as early as possible to avoid late enrollment penalties for Parts A, B and/or D.

Jeffrey Simpson · Answer

Yes, contact me to line up next steps for Medicare and SS registration. Not doing so may cause penalties and/or reduced income if not done in a timely, and knowledgeable, manner.

Denise Berg · Answer

Yes - you can sign up for Parts A and B 3 months prior to your birthday, the month of your birthday and the 3 months following your birthday. Once you have Parts A & B, you should work with an agent (there is no cost to you) to help you choose your best options, whether it is a Medicare Advantage plan or a Medicare Supplement plan, Hospital plan, Dental, Vision, and/or Hearing coverage.

Answered by Denise Berg on April 2, 2025

Broker Licensed in CO, AL, AZ & 15 other states

Answered by Denise Berg Medicare Insurance Agent

Amy Chamberlain · Answer

Well this would depend on if you have both Parts A and B. When people are still working and have Group Insurance most do not require you to have Part B. So when you retire then you would have papers to fill out by you and your employer to get your Part B going so you do not have a gap in coverage. This paperwork would be filed with the social security office.

Answered by Amy Chamberlain on March 25, 2025

Agent Licensed in MI & WI

Answered by Amy Chamberlain Medicare Insurance Agent

Gary Liesemeyer · Answer

Everyone's situation can be different.  I have been able to advise my clients how to best find the solution that works for them.

Brian Krantz · Answer

Yes — you’ll need to enroll to avoid late penalties. The timing matters, so let’s talk ahead of your retirement to make sure everything’s set up right.

Aisha Saleem · Answer

You should start learning about your benefits and options. You should enroll during your enrollment period to avoid penalties.

Barbara Barnes, CMIP® · Answer

Maybe.  It depends on what you've already done.

If you already chose your Medicare plans in lieu of a group plan at work, then you may be set and ready to roll.  But if you delayed your full Medicare enrollment because you had coverage at work, you will need to enroll in Medicare Parts A and B before you may choose any other plan options, like Medicare Advantage or Medicare Supplement.  It would also be a good idea to review any notices that you've received from your group plan to know where that plan stands in comparison to Medicare Part D and to see if you may owe a late enrollment penalty if the group plan was not as good as Medicare Part D.

Jill Belvin · Answer

If you are retiring and you are 65 or over 65 then yes you do need to apply for Medicare Part A (hospital) and Medicare Part B (doctor) coverage. You may need to apply at age 65 if your group workplace plan is not considered creditable coverage.

Answered by Jill Belvin on March 24, 2025

Agent Licensed in TX, AZ, FL, MI & NJ

Answered by Jill Belvin Medicare Insurance Agent

Adriane Williams · Answer

If you are turning 65 and or if you need to secure your healthcare coverage, yes! You can start preparing 3 months out. 

If you are retaining coverage with your prior employer, then no.

Gregory Dunham · Answer

That depends on your age (are you 65 or older, or do you have a qualifying health condition?) and what type of healthcare coverage you have been receiving.

If you are 65 or older, and leaving a company sponsored healthcare plan, you should review your Medicare options before retiring.

I’m retiring next year—do I need to do anything with my Medicare?

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