Medicare Expert Q&A: How Do I know When I'm Supposed to Enroll in Medicare?

Medicare won't automatically let you know when it's time to enroll. Medicare expert Christian Worstell answers the question of how and when to sign up.

In this Q&A series, Medicare expert Christian Worstell answers your questions about Medicare coverage, benefits, eligibility, enrollment and more. Christian is a licensed insurance agent and frequent contributor to

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"I am 64 and will be retiring next year. How do I know when I am supposed to enroll in Medicare?" – Ken S., Buffalo, NY

Hi Ken, and congratulations on your upcoming retirement!

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The time at which you will enroll in Medicare will depend on your age and circumstances. It’s important to note that depending on your situation, the Centers for Medicare & Medicaid Services (CMS) may not actually reach out and let you know that it’s time to enroll.

If you’re like most people, the first time you can sign up for Medicare is during your Initial Enrollment Period (IEP). This period begins three months before your 65th birthday, includes the month of your birthday and continues for another three months thereafter (for a total of seven months).

Even if you are still working when you turn 65, you may go ahead and sign up for Medicare during your Initial Enrollment Period. For more information on how Medicare may work with your employer coverage, you should speak with a representative from your Human Resources department.

  • Once you do retire (and are at least 65 years old and had group health insurance coverage through your employer), you should be given a Special Enrollment Period to enroll in Medicare Part A and Part B if you didn’t sign up during your IEP. This Special Enrollment period lasts for eight months

  • It’s advised that you also enroll in Medicare prescription drug coverage during this period, unless you have non-Medicare drug coverage that pays at least the same as Medicare drug coverage.

If your plans change and you retire before you turn 65, you will have to wait for your Initial Enrollment Period to begin before you sign up for Medicare. In the meantime, you may be able to purchase insurance coverage through the health insurance marketplace. 

If you are already collecting Social Security retirement benefits when you turn 65, you may be automatically enrolled in Medicare Part A and Part B (as long as you are a U.S. citizen or a legal permanent resident of at least 5 years).

If you are not yet receiving Social Security retirement benefits when you turn 65, you must manually enroll in Medicare Part A and Part B. You can do so online, over the phone or at your local Social Security office. 

How can I get help with Medicare enrollment?

Medicare enrollment can be confusing, but we’re here to help. Our Medicare Enrollment Guide provides much more information about enrollment periods and the sign up process.

You can also call to speak with a licensed insurance agent to learn more about Medicare Advantage plans and Medicare prescription drug plans, or you can compare plans online for free, with no obligation to enroll.

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Or call TTY Users: 711 to speak with a licensed insurance agent. We accept calls 24/7!


About the author

Christian Worstell is a licensed insurance agent and a Senior Staff Writer for He is passionate about helping people navigate the complexities of Medicare and understand their coverage options.

His work has been featured in outlets such as Vox, MSN, and The Washington Post, and he is a frequent contributor to health care and finance blogs.

Christian is a graduate of Shippensburg University with a bachelor’s degree in journalism. He currently lives in Raleigh, NC.

Where you've seen coverage of Christian's research and reports:

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