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65 and Still Working? Here’s What You Need to Know about Medicare Enrollment

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65 and Still Working? Here’s What You Need to Know about Medicare Enrollment

When it comes to birthdays, turning 65 is a big milestone. Not only is it traditionally considered the year in which Americans start their retirement, it also marks eligibility for health, hospital and prescription drug coverage through Medicare.

woman smiling while sitting at a table with a group of people

But what if you’re like many other people and plan to continue working, either out of choice or necessity? Well, as they say, “your mileage may vary.”

Medicare does not remind you to sign up on your birthday,1 so it’s up to you to understand when your eligibility begins.

Let’s take a closer look at what you need to know about Medicare enrollment as you prepare to blow out those 65 candles while remaining employed. (Happy birthday, by the way!)

Timing is everything

Remember: Your first Medicare Enrollment window typically opens three months before your 65th birthday and ends three months after your birthday month.

However, your enrollment period depends on your individual situation. Because Medicare includes several different enrollment scenarios for people working past their 65th birthday,2 what applies to your neighbor, friend or relative may not apply to you.

Enrolling at the right time matters. People who sign up for Medicare Part A (hospital insurance) and Medicare Part B (health insurance) after their initial enrollment period ends may incur penalties.3 Those penalties can cost you hundreds of dollars more each year for coverage — and you may have to pay the additional amount for as long as you maintain your Medicare benefits.

If you have employer-based health insurance

If you or your spouse are still working when you turn 65 — and you have health insurance through that job, you can delay your Medicare Part B enrollment without penalty until you or your spouse retire. If you lose that coverage, you can also apply for Part B without penalty.4

However, the options differ depending on the number of employees the company has as well as how your insurance coverage is provided.

  • If there are 20 or more employees, you can sign up for Medicare Part A when you turn 65 or later — as long as you’re not required to pay a Part A premium.
  • In some cases, your employer-sponsored policy might stop or limit coverage. If there are fewer than 20 employees, you (or your spouse) need to ask your employer if you need to enroll at 65.
  • If you or your spouse are self-employed or your employer’s health insurance isn’t defined by the IRS as an employer group health plan, you need to sign up for Medicare at 65.
  • If your employer gives you a stipend to purchase your own coverage, you’ll need to ask your insurer whether you should enroll5 for Medicare Part A and B at 65.

If you have COBRA

Do you anticipate turning 65 while relying upon COBRA to extend previous health care coverage? You need to enroll in Medicare Part B during the normal enrollment period (three months before and after your birthday month).6

Your COBRA coverage will likely end once you’re enrolled in Part B, which may save you money. But delaying Medicare Part B enrollment could leave you without coverage if you miss your initial sign-up window and your COBRA ends before the next enrollment period. You might also have to pay more for Part B coverage once you do enroll.7

If you’re working but have another type of health insurance

If you’re working and turning 65 with health coverage through Medicaid, a Marketplace plan or another source, Medicare offers guidance online — as well as a quick quiz — to help determine your timeline for enrollment.8

If you’re still working but don’t have health insurance

Get coverage and avoid late sign-up penalties by enrolling for Medicare Part A and Part B.9

Where to find Medicare Enrollment guidance and support

No matter what your work situation is at 65, it’s important to know all the facts about Medicare and be sure you enroll on time.

It’s also good to keep in mind that Medicare acts as a basic health plan — and you may have out-of-pocket expenses that aren’t covered.

That’s where a Medicare Supplement Insurance Plan can help.

Consider the approach of your 65th birthday as an opportunity to explore your Medicare choices and make the best decision to meet your needs.

Last updated April 2024.

Information in this article is general in nature and for your consideration, not as financial advice. Please contact your own financial professionals regarding your specific needs before taking any action based upon this information.

Not connected with or endorsed by the United States government or the federal Medicare program. This is a solicitation of insurance. A licensed insurance agent/producer may contact you.

RBFCU Investments Group LLC is a wholly-owned subsidiary of RBFCU Services LLC. RBFCU Services LLC is affiliated with Randolph-Brooks Federal Credit Union (RBFCU).

Medicare Supplement Insurance Plans, or Medigap Insurance Plans, and Medicare Advantage Plans are offered by certain agents of Randolph-Brooks Federal Credit Union (RBFCU) through PTT Financial, LLC, and not through or in association with Ameriprise Financial Services, LLC. Ameriprise Financial Services, LLC is not affiliated with PTT Financial, LLC.

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact or 1-800-MEDICARE to get information on all your options.

Each insurer has sole financial responsibility for its own products.


The following sources were last accessed February 2024.

1,6“Medicare: 3 Things to Consider before 65.”, Ameriprise Financial, 14 Dec. 2021,

2,4,5,9“Working Past 65.”,

3“Avoid Late Enrollment Penalties.”,

7“COBRA: 7 Important Facts.”,

8“When Can I Sign up for Medicare?”,