Medicare and Working Past 65

Do You Need to Enroll in Medicare?

It depends.  If you, or your spouse, are planning to work past 65, Medicare has specific guidelines that will dictate whether you can delay or you must enroll in Medicare Parts A and/ or B.

Simply, your decision regarding Medicare enrollment depends on the size of the employer that is providing your health insurance.

Determine Your Eligibility

If you receive group health insurance through your own or your spouse’s employment, below are the guidelines to determine if you can delay signing up for Medicare, or if you need to enroll when turning 65.

Employers with Under 20 Employees

If you, or your spouse, work for an employer with under 20 employees, generally you will need to enroll in Medicare Parts A and B during your Initial Enrollment Period (IEP).

Employers with 20+ Employees

If you, or your spouse, work for an employer with 20+ employees, you can delay your enrollment into Medicare Parts A and B. However, you can elect to drop your employer coverage for Medicare or have both employer coverage and Medicare.

TIP:  If you are able to remain on employer coverage after 65, you must confirm that your prescription drug coverage is considered “creditable” by Medicare.

How to Enroll when Working Past 65

You Work for an Employer with under 20 Employees

If you are required to enroll in Medicare because you work for an employer with under 20 employees, you should enroll during your Initial Enrollment Period (IEP).  To learn more about applying during your IEP, click here

You Work for an Employer with 20+ Employees

If you delayed enrollment in to Medicare and remained on your large employer coverage, you can enroll in Medicare Parts A and B during a Special Enrollment Period.  

Applying for Part A

If you delayed enrollment into Part A because you funded a Health Savings Account, there are three ways you can apply.

Important Note:  Medicare will backdate your Medicare Part A start date 6 months from the date of your application. This is an automatic default and you cannot avoid this. So It is very important that you coordinate your enrollment into Part A and the termination of your HSA contributions to avoid any tax violations.

✓ Enrollment Option #1 – Apply online (recommended)

  1. Create an account ( and select “Apply for Medicare Only.”
  2. Log in to your newly created account.
  3. Click on “Apply for Medicare Benefits.”
  4. Review pre-populated information for accuracy.
  5. Complete the signature process (we recommend you use a personal email account).
  6. Look for your enrollment confirmation in your email inbox. 

✓ Enrollment Option #2 – Apply in person

  1. Locate your local SSA office. Click link below to find the office closest to you:
  2. You can call the Social Security Administration at 1-800-772-1213 to schedule an appointment.

✓ Enrollment Option #3 – Apply via phone 

You can call the Social Security Administration at 1-800-772-1213 to schedule an appointment to complete your application for Part A over the phone.  

Note: Appointments are not immediate and you will receive a future appointment call date, which could be 30-60 days in the future. Therefore, pay close attention to your appointment date and your desired Medicare start date so you can avoid lapses in coverage.

Applying for Part B

If you delayed enrollment into Medicare Part B because you had employer coverage, you can apply during a Special Enrollment Period, which lasts 8 months from your last date of employer coverage. 

NOTE: We recommend applying 60-90 days prior to your loss of employer coverage to avoid any gaps in coverage. 

You can only apply online or in-person because you will need two forms, the 40B and a CMSL-564, to successfully apply for Part B. 

Required Forms for Part B Enrollment

CMS L-564 – This is a form your employer completes that confirms your health insurance since turning 65. This form creates your special enrollment as well as allows you to avoid any late enrollment penalties for not enrolling when you turned 65.

CMS 40B – This is your request for Medicare Part B. Note: In the remarks section, you need to write in the month you want your Part B to begin. Not doing so would default enroll you in the nearest month, which often is before you need it. 

✓ Enrollment Option #1 – Apply online (recommended) 

  1. Go to:
  2. Complete all required information and sign (we recommend you use a personal email account).
  3. Write in your “desired coverage effective date” in the “Remarks” section A#7. Example: Desired coverage effective date January 1, 2022.  Note: it is important to input the date that you are requesting your Medicare coverage to start, or it will default to the first day of the following month. 
  4. Provide a completed form CMS-L564 or copies of a recent pay stub, ID card or tax return to complete the application process.
  5. Check your email inbox to verify and complete the Part B online application process.

✓ Enrollment Option #2 – Apply in person

  1. Complete forms CMS-L564 and Medicare 40B.
  2. Locate your local SSA office by clicking the link below:

Creditable Employer Drug Coverage

It is important that you maintain creditable prescription drug coverage when employed, or you could be penalized later when you enroll in Medicare prescription drug benefits. 

What is Creditable Coverage?

Creditable coverage is Medicare-approved employer health insurance coverage that pays on average as well as the Medicare standards for prescription drug coverage. 

If your coverage is not creditable, you would need to apply for a prescription drug plan during your Initial Enrollment Period.  Note: You would need to enroll in Medicare Part A or B to get a Part D plan. 

What is the Notice of Creditable Coverage?

Annually, your employer or health insurance provider will send you a Notice of Creditable Coverage to help you monitor your prescription drug plan’s status.  This notice works as proof that your current coverage is creditable when you first become eligible for Medicare. Keep the notice as you might need it if you decide to join a Medicare drug plan later.

Medicare and Employer Health Plans

It is important to understand that COBRA after age 65 works differently than before age 65.  Specifically, after age 65, COBRA cannot be the primary payer of claims, nor is considered creditable coverage for Medicare Part B.

The way COBRA works after age 65 is dependent on your Medicare eligibility and enrollment status. There are numerous scenarios relating to COBRA and Medicare and each is detailed below.

Note:  The rules for COBRA and Medicare apply regardless of who is paying for COBRA.  For example, if part of a separation agreement includes paying for COBRA premiums by the employer, this will not change the way the COBRA guidelines are interpreted and enforced.

Medicare and Turning 65

If you did not have Medicare Parts A and/or B prior to being offered COBRA, once you enroll in Parts A and B, your COBRA will be cancelled.

A common example is an employee turning 65 and on COBRA. Their enrollment into Medicare is mandatory because Medicare becomes primary when they turn 65. All COBRA benefits would be terminated upon their enrollment into Medicare.  This individual would want to apply for Medicare during their Initial Enrollment Period.

Medicare and Working Past 65

If you worked past 65 and is offered COBRA, there are a few scenarios.

  • You have Medicare Part A only and is offered COBRA. You would want to enroll in Part B immediately because Medicare becomes your primary payer in this scenario.  COBRA would act like a Medicare Supplement and pay after Parts A and B, as well as provide Part D equivalent coverage for prescription drug needs.
  • You have Medicare Parts A and B before offered COBRA. COBRA would become the second payer behind Medicare, as well as provide Part D creditable coverage for prescription drug benefits. You can remain on COBRA for up to 18 months, however, when reaching the end,  you would have to apply for individual Medicare plans including Part C, Part D and Medicare Supplement.

Note:  COBRA is considered creditable coverage for Part D. Remaining on COBRA will not place you in a penalty situation with Medicare. However, whenever you leave the COBRA plan, you have 2 months from the end of the coverage to enroll in a creditable Medicare Part D plan.

If you are planning to work past 65 and will receive your health insurance benefits through a high deductible health plan with a health savings account, it is important to understand how this impacts your Medicare enrollment decisions. 

What you need to know is that enrolling in Medicare, Parts A and/or B, will negate your ability to fund your Health Savings account. This is because Medicare Parts A and B do not meet the criteria to qualify as a high deductible health plan. So funding the HSA will create a tax penalty situation.

If you have an HSA and are considering enrolling in Medicare, it’s important to plan accordingly. 

You can still use your HSA funds to pay for out-of-pocket Medicare expenses, such as deductibles, copays, and premiums. However, you’ll need to stop contributing to your HSA once you enroll in Medicare to avoid penalties.

When you retire, you are required to complete a series of steps to successfully transition from the group health plan into Medicare.

Note:  Applying for Part A after age 65 will automatically backdate your Part A coverage 6 months from the date of the application.  This can have a significant impact on HSA contributions.

Important:  When transitioning to Medicare, you are enrolling under an individual status, which could impact any dependent group health coverage. 

Your SEP To-Do List When Working Past 65

Determine your eligibility for a Special Enrollment Period.

Discuss with your employer how your group plan coordinates with Medicare. 

Determine when your current coverage ends to avoid coverage gaps.

Determine what documentation is required to qualify for an SEP.

Apply for your applicable Medicare benefits based on the applicable timelines.

Determining SEP Eligibility

Not sure if you’re eligible for a Special Enrollment Period when working past 65?  Let us help you.  We can explain when and how you’ll need to enroll to have the coverage you need, when you need it, without late penalties.

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