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What You Need to Know Before You Enroll in Medicare


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. 31.

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!

How to Enroll in Medicare Checklist

Stop your Health Savings Account contributions.

Basically, there are two situations in which both the employer and employee need to stop making contributions to the health savings account (HSA).

If you apply for Medicare before your 65th birthday month, you can continue to contribute to your HSA with your employer through the day prior to your Medicare effective date. Once you apply for Medicare, you can no longer receive new HSA deposits from your employer. However, you can use your existing HSA funds to pay for approved expenses.

The second situation is if you decide to work beyond age 65 and take Medicare later. You will need to stop those contributions six months prior to applying for Medicare. Otherwise, you could be subject to penalties. Learn more here.

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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