When to Enroll in Medicare

Deciding when to enroll in Medicare can be one of the most confusing Medicare decisions to make. Sure, its straightforward when you are turning age 65, but what if you are going to continue to work? Let’s explain.

Starting Medicare Before Age 65

Some people qualify for Medicare before age 65 through disability. If you qualify for disability you will receive Part A immediately and then receive Part B 24 months later. This all happens automatically.  

Starting Medicare At Age 65

Most people will begin Medicare when they turn 65, but others will continue working and stay on their employer group health insurance.

Not On Employer Group Health Insurance

Congratulations, your enrollment into Medicare is the simplest. Your Initial Enrollment Period (IEP) is a 7-month period that spans 3 months before and after the month you turn age 65. 

Example: Initial Enrollment Period at Age 65:

  • Cindy turns age 65 on June 23rd, 2025

  • The earliest her Medicare can start is the first day of her birth month – June 1st

  • Her IEP begins March 1st (3 months before June 1st)

  • Her IEP ends September 1st (3 months after June 1st)

  • If she enrolls before June 1st (recommended) her start date will be June 1st.

  • If she enrolls after June 1st through the end of her IEP, coverage will start the first of the next month.

Good to know tidbit:
If your birthday is on the 1st of the month, you’ll start Medicare on the 1st of the previous month. Example: John turns 65 on June 1st, 2025. His Medicare starts May 1st.

Continuing to Work

Many people work past age 65, since full retirement age for Social Security Benefits has been raised to 67. The rules for signing up for Medicare are different based on the size of your employer group health plan:

  • Under 20 employees – Medicare is primary, employer coverage is secondary. You will have to take Medicare Part A and Part B in order for your coverage to work properly.

  • Over 20 employees – Employer coverage is primary, Medicare is secondary. Often you will want to delay sign up for Medicare if you will be staying on your employer health coverage. However sometimes Medicare coverage is better / cheaper than employer coverage so you’ll want to compare your options.

Starting Medicare After Age 65

If you continued to work past age 65, you will need to enroll in Medicare once you retire and lose your employer group health insurance.  We recommend applying 2-3 months in advance of your retirement.

Your Initial Enrollment Period will work just the same as if you had started Medicare at age 65, but instead of your birth month being the start date for Medicare, you will start Medicare when your employer coverage ends. Make sure to confirm with HR when your work coverage will end. Most, but not all, will cover you until the end of the month.

Example: Initial Enrollment Period after age 65

  • Lisa is retiring and losing employer coverage on June 30, 2025

  • The earliest her Medicare can start is July 1st.

  • Her IEP begins April 1st (3 months before July 1st)

  • Her IEP ends October 1st (3 months after July 1st)

  • If she enrolls before July 1st (recommended) her Medicare start date will be July 1st.

  • If she enrolls July 2nd through the end of her IEP, Medicare coverage will start the first of the next month.

Check out our Guide About How to Sign Up For Medicare Here

FAQs

What Happens If I Don't Enroll in Medicare? Do I Have to Sign Up?

  • No, you don’t have to enroll in Medicare. No one will make you. But if you don’t you’ll lack coverage you might need.

Will I Be Penalized If I Don't Sign Up For Medicare?

  • Yes. Not signing up when you turn 65 / retire can cause you to be penalized for the rest of your life. Late Enrollment Penalties can add thousands of dollars per year to the cost of your Medicare coverage, and never go away.

Will I Be Penalized If I Delay Medicare to Keep Working?

  • No, as long as you are covered by your employer plan or your spouses employer plan, and you or your spouse are actively working, and the coverage is considered “credible” in the eyes of the government you will not be penalized.

Should I Keep My Employer Group Insurance or Take Medicare?

  • It depends. Sometimes employer coverage is better, meaning you should delay taking Medicare. But sometimes Medicare coverage will be cheaper and better than your work coverage. We often compare this for our clients.

Summary

Knowing when to enroll in Medicare can be a confusing situation. The key is to make sure you have “creditable coverage” so that you avoid any unnecessary penalties. Schedule an appointment with us to compare the plans in your area.