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How to Enroll in Medicare

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Medicare can be complicated, but we're here to help you simplify it. This is Medicare enrollment explained in one minute.

An individual can have a number of different enrollment periods that they can take advantage of.

Your Initial Election Period revolves around a seven-month window, around your 65th birthday. Three months prior, the month of, and three months after.

A person can also enroll in Medicare with a Special Election Period. That is when they're coming off an employer-based plan, and they're older than 65.

Once eligible for Medicare, you can also change your Medicare plans during the Annual Election Period, which happens from Oct. 15 until Dec. 7, every year, and that gives people a Jan. 1 effective date on any changes.

A person can be enrolled in Medicare automatically if they're receiving a Social Security check prior to 65. Then at 65, their Medicare would automatically start on the 1st day of the month of their 65th birthday.

If you have questions about your Medicare enrollment, call us. We've helped over 50,000 people just like you, with these same types of questions. You'll be glad you did.

Are you planning to enroll in Medicare in the near future? If so, you have several factors to consider as you decide on the details. Whether you’re enrolling when you are first eligible at age 65 or signing up later, you can use this checklist as a starting point!

How to Enroll in Medicare Checklist


Retirement isn’t a requirement.

You can enroll in Medicare and continue working full-time or part-time. If you plan to work past age 65, your enrollment may be impacted by the size of your employer.

Learn more about whether you’ll be required to enroll at age 65 if you continue working.

There are multiple enrollment periods.

Initial Enrollment Period

Your Initial Enrollment Period (IEP) is a seven-month window when you are first eligible for Medicare. It centers around your birth month, beginning three months before it and ending three months after it. For example, if your 65th birthday is Nov. 20, your IEP would begin on August 1 and end on Feb. 28.

Annual Enrollment Period

Medicare’s Annual Enrollment Period (AEP) is open from Oct. 15 to Dec. 7.  Once you enroll in Medicare, you can make changes to your coverage between these dates that go into effect the following year. AEP is open to anyone currently on a Medicare plan.

Special Enrollment Period

You may also qualify for a Special Enrollment Period (SEP) based on certain events or circumstances—for example, if you lose your employer or spousal coverage unexpectedly. You can qualify for an SEP for various reasons, so we recommend contacting our team for advice on your specific situation.

Your Social Security Status

If you are already drawing Social Security ahead of your 65th birthday, you don’t need to take any action to enroll in Medicare. Social Security will automatically sign you up for Medicare Parts A and B. If you need additional coverage, such as a Medicare Supplement or Medicare Advantage plan, you can contact our advisors for a customized list of options.

If you are not yet drawing Social Security, you can start withdrawing ahead of when you’ll need Medicare coverage. This will result in Social Security enrolling you automatically. You can also continue to delay your Social Security payments and sign up for Medicare another way. Our advisors can help you enroll at no cost!

Your Health Savings Account Contributions

If you have a health savings account (HSA), you may need to stop your contributions up to six months in advance, depending on when you enroll in Medicare. Otherwise, you could be subject to penalties. You can still use the funds you already have saved for qualified Medicare expenses, even after you’re on a Medicare plan.

You have hundreds of options.

Between Medicare Advantage and Medicare Supplement plans, hundreds of plans options are out there if you want to purchase additional coverage. If you need help with your health insurance in Ohio, Kentucky, Indiana, or Florida, our local advisors can help you compare plans and find the right fit.

Enroll in Medicare with a local expert.

You aren’t alone in the search for the right plan. Our advisors are with you at every step, from researching plan options to enrollment and beyond. Reach out to us for no-cost guidance on your health insurance in Ohio, Kentucky, Indiana, or Florida! You can call 937.915.3563 or email to get started.

Already a RetireMed client? You can call your client advisor team at 877.222.1942 or email

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