Helping You Understand The A, B, C’s and D’s of Medicare.

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CALL: 1.800.936.5165

How to Enroll In Medicare

Learn more about how to enroll in Medicare below or click for your FREE no-obligation consultation.

Medicare Enrollment

Medicare enrollment could be automatic for some people, while for others, it generally depends on when they turn 65 or how they become eligible for Medicare.

If you are eligible, you can enroll for Medicare in several ways.

● Online at
● Call Social Security at 1-800-772-1213.
Medigap Supplement Headquarters will consult you to determine your eligibility and guide you through the enrollment process.

Click here to review what is required to qualify for Medicare.



You can register for Medicare in person by:
● Visit your local Social Security office
● Contact the Railroad Retirement Board to speak to a representative who will help you register for Medicare.

There are some situations where you may be enrolled for Medicare automatically.
For example, if you receive Railroad Retirement Board benefits or Social Security benefits, you will automatically enroll for Medicare when you turn 65.



If you already receive disability benefits when under 65, either from the Railroad Retirement Board or Social Security, you will automatically be enrolled in Original Medicare once you have received disability benefits for more than 24 months. People who have ALS will automatically be enrolled for Original Medicare the same month they receive disability benefits.



Medicare enrollment is not automatic for some people. If you fall in this category, you will need to manually enroll as soon as you become eligible to avoid paying the late enrollment penalty.

You can enroll for Medicare during the Initial Enrollment Period. The Initial Enrollment Period starts three months before you turn 65 and lasts until three months after you turn 65.

You can enroll for Medicare during the Initial Enrollment Period if:
● You are not receiving retirement benefits
● Are close to turning 65
● You have turned 65

You will not be enrolled in Medicare automatically if you do not qualify for retirement benefits from the Railroad Retirement Board or Social Security.

You will also need to enroll for Part A and Part B during the Initial Enrollment Period. You can also enroll for Medicare during the General Enrollment Period if you failed to register when you were first eligible. However, you will pay a late enrollment penalty for Original Medicare.


Under some special circumstances, you may be eligible to enroll for Medicare during the Special Enrollment Period.

You can delay Medicare enrollment without facing the late enrollment penalty if:
● You are still working and you have employer health insurance
● You are covered under your spouse’s health insurance.

Understanding the requirements to be eligible for Medicare and how to enroll can be a complicated process. However, at Medigap Supplement Headquarters, we can help simplify the process. Contact us today to get your questions answered.

Get The Right Medicare Plan Today

Dale Wondisford


15 Years experience helping hundreds of families get the best insurance policy to meet their needs.


Fill out the form to get your questions answered by Dale Wondisford wih a FREE no-obligation consulation.

laina roy
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I have had the opportunity to have meet Dale approximately 7 years now. I have never had someone take the time to check what’s the best way to insure myself. He does a very in depth review of what was going on with health issues and the medications, in order to place me with an insurance that’s going to save on my costs
Mark Poff
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Dale is very knowledgeable and experienced working with the many offered medicare plans finding the best plan that benefits his clients which he did for my wife and I. I highly recommend Dale as I totally respect his judgement of which plan is best for the client.
Richard Hibbard
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Dale is really helpful he will get you a answer to any questions you may have. He even got on a three way call so we could hear what was going on. He always returns your call promptly. Dale is very knowledgeable about all types of insurance. Very friendly and no pressure tactics to buy. Would highly recommend Dale.