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How Do I Find Medicare Enrollment Help?

Updated: Oct 28, 2023

Find Medicare Enrollment Help

Turning 65 and getting on Medicare for the first time can be confusing. You want to make sure you enroll at the right time, choose suitable coverage, and avoid costly mistakes. For assistance navigating your Medicare options, several excellent national and local resources provide knowledgeable support. This article outlines where to turn to get clear answers to your Medicare questions and smooth guidance through the enrollment process.

State Health Insurance Assistance Programs (SHIPs)

Every state has a State Health Insurance Assistance Program (SHIP) that provides free counseling on Medicare. SHIP counselors are trained specifically on Medicare and can help with:

  • Answering questions about Medicare rules, coverage, costs, and claims

  • Explaining the differences between Original Medicare, Medicare Advantage, Part D Plans, and Medigap

  • Comparing plans and options to suit your needs

  • Enrolling you in Medicare Plans

These local programs go by different names like HICAP (Health Insurance Counseling and Advocacy Program) in California and SHINE (Serving Health Insurance Needs of Elders) in Florida. But they all aim to help people understand and enroll in Medicare coverage.

SHIP counselors are available for one-on-one sessions either virtually or in person. Find contact information for your state SHIP at or call 1-877-839-2675. is the official federal Medicare website. It offers a wealth of information about Medicare eligibility, enrollment periods, plan choices, costs, and benefits. If you have general Medicare questions, the website likely has the answers you need.

Key resources on include:

  • Details on the different Parts of Medicare (Part A, Part B, Part C, and Part D)

  • A Find Plans tool to compare Medicare Advantage and Part D Plans in your area

  • Cost calculators to estimate your premiums and out-of-pocket expenses

  • Instructions for how to enroll both online and through Social Security

The site also has a “Talk to Someone” section where you can live chat with a Medicare representative or call 1-800-MEDICARE (1-800-633-4227) for personalized help. Multilingual assistance is available.

Social Security Offices

Though Medicare is run by the Centers for Medicare & Medicaid Services, enrollment is handled by the Social Security Administration. Your local Social Security office can answer questions about:

  • When and how to sign up for Medicare

  • Eligibility for Medicare Savings Programs to help pay costs

  • Applying for Extra Help to cover Part D prescription drugs

To find a Social Security office near you, call 1-800-772-1213 or search on You can also enroll in Medicare through your local Social Security office, not just online.

State Insurance Departments

If you want help understanding Medigap policies or Medicare Advantage Plans available in your area, contact your State Department of Insurance. They regulate insurance carriers in your state and publish information about the plans sold in your region.

Look up your state medical insurance department through the National Association of Insurance Commissioners at Check available resources and reach out with questions about advising on local Medicare options.

Medicare Rights Center

The Medicare Rights Center is a national nonprofit organization that runs a Medicare helpline where counselors answer questions about Medicare coverage at no charge. They can help with topics like:

  • Deciphering your Medicare Plan choices

  • Understanding enrollment windows and deadlines

  • Navigating Medigap, Medicare Advantage, and Part D Plans

  • Appealing denied claims or coverage

Reach their helpline at 1-800-333-4114 or visit their website at to learn more about Medicare.

AARP Resources

AARP offers Medicare guidance both through local offices and national help lines. Members can discuss Medicare with advocates and use tools to compare plans.

Key resources include:

  • AARP MedicareHelp line at 1-877-926-8300

  • Medicare QuickStart Guide with enrollment checklists

  • Medicare comparison tools to shop plans

  • Local seminars, webinars and meetings with Medicare experts

Non-members can call AARP to enroll and access these benefits for $12-16 per year. Visit for more.

Medicare Publications

CMS publishes a variety of helpful guides explaining Medicare that you can reference. These include:

Medicare & You Handbook: Mailed to all Medicare households annually. Outlines Medicare benefits, rights, choices, plan options, and costs in detail.

Choosing a Medigap Policy: Explains what Medigap covers, policy types, and how to enroll.

Medicare Advantage Plans: Details Medicare Advantage, costs, benefits, and how these plans work.

View and download these publications for free at or request printed versions by calling 1-800-MEDICARE.

Additional Support Options

Beyond the resources above, you may find help through:

  • Doctors/Health Providers: Ask your doctor questions about Medicare and the plans they accept.

  • Caregivers: If you have an in-home caregiver, they may be knowledgeable about Medicare to help guide you.

  • Community Centers: Local senior centers often have seminars on Medicare enrollment.

  • Churches: Places of worship may offer Medicare counseling or connect you with resources.

  • Friends and Family: People you know on Medicare can share their experiences and advice.

  • Private Brokers: Brokers can advise you, but may charge fees or steer you toward specific plans. Be cautious.

The key is finding objective, unbiased support from counselors well-versed in Medicare. Use the trusted resources in this article to ensure you make informed choices about your coverage and fully understand your rights. With proper help, you’ll smoothly transition onto Medicare and choose cost-effective plans that provide the health coverage you need.

Medicare Enrollment Help Step-By-Step

Here is a step-by-step guide on how to get enrollment help for navigating your transition onto Medicare:

1. Determine Your Initial Enrollment Period

Know when you’ll be eligible for Medicare and can start enrolling. Most commonly this is three months before your 65th birthday through three months after. If you have disability, there are different timelines. Understand your initial enrollment window.

2. Review the Medicare & You Handbook

This guide will be mailed to you and is also available online. It provides an excellent overview of how Medicare works, what’s covered, enrollment periods, and your plan choices. Study it to get educated.

3. Contact Your State SHIP Program

Get free Medicare counseling from your State Health Insurance Assistance Program. Meet with a SHIP counselor early on to discuss your specific situation and plan options.

4. Research Plans on

Use Medicare’s Plan Finder tool to see what Medicare Advantage, Part D, and Medigap Plans are available in your area. Compare costs and coverage.

5. Call 1-800-MEDICARE

Use Medicare’s helpline to get answers to any additional questions after reviewing materials and plans available. Speak with a Customer Service Representative.

6. Meet With a Social Security Representative

Visit your local Social Security office where you can enroll in Medicare parts A and B. Ask any other questions before you submit your enrollment forms.

7. Choose and Enroll in Plans

With the help of a SHIP counselor and your own research, choose plans that best match your needs. Formally enroll by the end of your Initial Enrollment Period.

8. Seek Follow-up Support as Needed

If any other questions or issues come up, don’t hesitate to contact SHIP counselors or Medicare helplines for continued support.

With these steps, you’ll work with knowledgeable advisors who will answer your Medicare questions and simplify the enrollment process. You’ll feel confident you made smart Medicare coverage choices.


Turning 65 and navigating Medicare choices for the first time is a major milestone. But you don’t have to figure it all out alone. Tapping into free counseling through State Health Insurance Assistance Programs provides a valuable service to help you make smart Medicare decisions. Combined with your own research using official Medicare resources, you can take an informed approach to choosing the right Medicare coverage. Seek help early and often from these trustworthy sources so you can enroll in Medicare with confidence. With the proper guidance, you’ll smoothly transition onto Medicare and set yourself up for healthcare coverage that best fits your needs and budget, both now and in the future.

We’re Here to Help

You do not have to spend hours reading articles on the internet to get answers to your Medicare questions. Give the licensed insurance agents at Lane Financial Strategies a Call at (804) 897-2170. You will get the answers you seek in a matter of minutes, with no pressure and no sales pitch. We are truly here to help.


When do I need to sign up for Part B?

If you get disability benefits from Social Security, you'll need to sign up during your Medicare enrollment period which starts 3 months before your Medicare coverage starts and ends 3 months after the month you turn 65.

How do I get help with my Medicare enrollment?

You can get free Medicare enrollment assistance and counseling from your state health insurance assistance programs. Many states call their programs the Health Insurance Counseling and Advocacy Program.

When does my Medicare coverage start?

If your 65th birthday falls on January 1st, February 1st, or December 1st, your coverage starts on the first day of the month you turn 65. For other months, coverage starts on the first day of the month after your birthday.

Can I get any financial help with paying for Medicare costs?

Yes, there are certain Medicare savings programs available for people with limited income and resources. Contact your state health insurance assistance program counselor to learn more.

How do I sign up and get my medicare card?

The easiest and fastest way is to visit the Welcome to Medicare website and create your secure my account. You can sign up and get your Medicare card digitally through your account.

What if I live in Puerto Rico, Guam or the U.S. Virgin Islands?

The rules and deadlines for signing up for Medicare may be different if you live in Puerto Rico, Guam or the U.S. Virgin Islands. Contact your local Social Security office for information about signing up in those locations.

I already have Part A. Do I need to sign up for Part B in 2022?

If you already have Part A, you don’t need to sign up for it. However, if you want Part B medical insurance coverage to begin on January 1st, 2022, you'll need to sign up for Part B during the fall open enrollment period which runs from October 15th to December 7th, 2021.

What is the talk to someone option on the Medicare website for?

The "Talk to Someone" option allows you to chat with a Medicare counselor or call Medicare's toll-free helpline to ask questions about Medicare rules, coverage, claims or choosing a Medicare health or drug plan.

How do I choose a Medicare health plan?

Start by visiting the website to help you understand your options. Speaking to a counselor from your State Health Insurance Assistance Program can also help you understand the differences between Medicare Plans and choose one that works best for your situation and health needs.

When does my Part A coverage start if I have ALS?

If you're diagnosed with Lou Gehrig's disease (ALS), your Medicare Part A and Part B coverage can start 24 months from the date you become entitled to Social Security disability benefits. Contact your local Social Security office for more details.

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