Medicare 101

Medicare Checklist

Christian Worstell

by Christian Worstell | Published September 16, 2020 | Reviewed by John Krahnert

Medicare is a complex program, and signing up can be confusing.

As you gear up to enroll in Medicare, use this handy checklist to help you stay on top of enrollment and make the process a little easier.

Doctor with clipboard

Six Months Before You Turn 65:

Understand how Medicare works.

Three Months Before You Turn 65:

Enroll in Medicare.

  • Enroll in Original Medicare during your Initial Enrollment Period, which begins three months before your 65th birthday, includes your birthday month and extends three months after your 65th birthday

  • Apply for Medicare online through the Social Security Administration

  • Apply for Medicare by phone by calling 1-800-772-1213, Monday through Friday, 7AM to 7PM

  • Apply for Medicare in person by visiting your local Social Security office

  • When you apply for Medicare, make sure you have the following information ready:

    • Date and place of birth

    • Medicaid number and Medicaid start/end dates (if applicable)

    • Current health insurance information

  • After you enroll in Medicare Part A and Medicare Part B, you can join a Medicare Prescription Drug Plan (Medicare Part D) and/or a Medicare Supplement Insurance plan

You can compare Part D plans available where you live and enroll in a Medicare prescription drug plan online when you visit

Make sure you sign up on time. This is the most important part of signing up, because if you delay enrollment for too long, you could end up paying a late enrollment penalty for as long as you have Medicare.

After You Enroll in Medicare:

Pull together resources that can help guide you from enrollment to next steps.

  • Find area-specific information through your State Health Insurance Assistance Program (SHIP), a free counseling service

  • Visit the website to view or print the Medicare & You 2020 Handbook for information on everything Medicare-related

Print out the following checklist and hang it on your refrigerator to remind yourself of all of the important deadlines.

If you need help covering some of your Medicare out-of-pocket costs, Medicare Supplement Insurance (Medigap) can help.

To enroll in Medigap, call today to speak with a licensed insurance agent who can help match you to a plan that makes sense for you.


Find Medigap plans in your area.

Compare Plans
Or call 1-800-995-4219 to speak with a licensed insurance agent.


Christian Worstell is a health care and policy writer for He has written hundreds of articles helping people better understand their Medicare coverage options.

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