Medicare and Working Past 65

By planmedicare1 - April 9, 2021

The 2021 workforce in America has an increasing share of workers who are 65 and older. In fact, the U.S. Bureau of Labor Statistics is predicting that the segment of workers 65 to 74 years old to increase over 30% in 2026. The fact is- people are retiring later in life.

For many, retiring young, is not financially feasible,  and for others it is about fulfillment and not being ready to hang up their hats.

If you are planning to remain in the workforce beyond 65, irrespective of why, you do not want to overlook navigating your Medicare enrollment options before or after retirement.

When you turn 65, it’s important to evaluate all of your options. Your Medicare enrollment choices will depend largely upon your company’s size and what kind of health benefits you have and want to have as you go forward. It’s important to understand the factors you must consider when turning 65, and what you need to do to ensure proper Medicare coverage.

Should I Delay Medicare Benefits?

The decision to enroll in Medicare when you turn 65 and are still working, depends on the size of the company you work for. The decision to delay Medicare enrollment is not a blanket one-size-fits-all answer.

If you (or your spouse) work for an employer with 20 or more employees and you are signed up for their group health plan, you are allowed to delay Medicare until you retire without any cost penalties. This is due to a rule called Creditable Coverage.

In contrast, if you work for a company with less than 20 employees, you can not delay enrolling in Medicare, and if you do- you will face costly penalties. . Even if you have group coverage, you will want to apply for Medicare and enroll in Parts A and B to avoid penalties (you also must consider if you have an HSA),  Medicare will be primary, and your group coverage will be secondary.

However, many group coverage plans offer prescription drug coverage. Should you choose to keep your small employer group coverage, you may be able to delay a Prescription Part D Plan enrollment, if the group plan offers one.

Always do a cost comparison to see if it is financially worthwhile to keep or drop your group coverage while on Medicare.

How do I enroll in Medicare When I’m ready to Retire?

If you are eligible to delay Meidcare and stay on your employer coverage past 65, you will be able to enroll in Medicare at any point that you decide to retire, under a different enrollment process. The Initial Enrollment Period (IEP), is available to people who are turning 65 or have just turned 65 (3 months prior to and after your 65th birthday). Should you stay on employer coverage, your enrollment period will be different, it will be considered a Special Enrollment Period (SEP), and you will be able to enroll in Part B at any point after you retire.

Should I Enroll in Medicare Part A Regardless of my Employment Status?

The short answer is, yes, most likely you qualifiy for premium – free Part A, based on your work history (but irrespective of your employer size). Part A is recommended because there is no additional cost implications and it can help with certain costs when enrolled in a larger employer plan.

You can enroll in Medicare Part A online at You can apply for Part A online at You’ll complete an online form, with the option of delaying Part B if you choose to stay on an employer plan and you will have creditable coverage.


What about Medicare Part B?

As discussed, if you qualify with creditable coverage, you can delay your Part B until after retirement, past the age of 65. The SEP for retirement is an 8 month window in which you are eligible to enroll after you retire, and it begins on the day you lose your employer coverage or you choose to retire.

In order to enroll in Part B during the retirement SEP, you must fill out forms that your employer must also complete. These need to be submitted to Social Security in order to verify you had creditable coverage under the employer plan.  These forms include:

  • Form CMS-40B – Paper application for Part B
    • You will complete this with the necessary information to apply for Part B
  • Form CMS-L564 – Request for Employment Information
    • This form is for your employer to complete, attesting to your dates of creditable coverage.

You can either mail or take these forms in-person to your local Social Security Office.

How do I Enrolling in a Medicare Supplement insurance after 65?

If you want to enroll in a Medicare Supplement Plan when you retire after the age of 65, you can choose to do so at the same time as your Part B enrollment window. The window to enroll in a Medicare Supplement plan is 6 months and it starts the day that you Part B coverage starts.

During this time, you should reach out to the advisors at Plan Medicare to select the best Supplement coverage that fits your needs and benefits.  You will be able to choose a Medigap plan at the best rate regardless of your health. You cannot be turned down for a plan in this enrollment period, so it is important you don’t let it pass you by.


How do I Enroll in a Medicare Advantage plan after working past 65?

To enroll in a Medicare Advantage Plan (MAPD), you must have Part A and Part B. Just as you did with the other parts of Medicare, you will have an SEP in which you can enroll. For MAPD plans, this is a 2-month window of time beginning the month you no longer have employer coverage.


Deciding on what to do with your Medicare insurance when you turn 65 and are still working is very confusing. Speak with our team to learn about your specific local and personal options so you can make informed and educated Medicare decisions.

Speak to a Licensed Advisor in Medicare today

Book an Appointment Call: 516-900-7877