The Medicare Pathway

  1. You can begin Original Medicare (Part A & B) coverage as early as the first of the month before when you turn 65* OR after 24 months of Social Security Disability Income. Sign up for Original Medicare three months before and after your initial eligibility date. Click here.
    *which means that if your birthday IS the first of the month, Medicare can begin the first of the PRIOR month if you sign up in a month at least two months prior.
  2. If you will still be working AND still be eligible for your employer’s (or your spouse’s employer’s) group health plan when turning 65.
  3. Later, you can sign up for Original Medicare (Parts A & B or B if you already have A) with an allowed Special Enrollment Period (SEP). You can learn more about Valid SEPs and how to sign up by clicking here.
  4. If you missed your enrollment period, you can enroll during the General Enrollment Period (Jan 1 to Mar 31), but you will pay a lifetime Late Enrollment Penalty

Your Medicare Enrollment Pathway begins 4 to 6 months before eligibility and will involve different steps depending on your circumstances. 

Once you sign up for Medicare, you can check the status of your Medicare application by clicking here.

Original Medicare (Part A & B) eligibility beings on the first of the month in the month you’ll turn 65 or after 24 months of Social Security Disability Income. 

Your Medicare Enrollment Pathway begins 4 to 6 months before eligibility and will involve different steps depending on your circumstances. 

 We recommend, as your first step on the pathway, that you attend our monthly Medicare Seminar/Webinar

To learn more about the process, when to do what, and what your options are. Working with Wheelers is not an additional cost, so hopefully we can save you some time and money. 

We'll discuss original Medicare (Parts A &B), Part C (Medicare Advantage), Part D (Drugs Plans), and Medicare Supplement.


  • October 2nd in South Paris at 5pm 
  • October 5th in Bethel at 5pm
  • Oct 4th in Buckfield at 630pm
  • OHCHS on Oct 11th at 630pm

Register by emailing mike@wheelersinsurance.com!


If you are a subscriber to an Individual Health Plan, you are no longer eligible for a Premium Tax Credit once you become eligible for Medicare.  

If you are the sole subscriber under the policy, the policy should be canceled at the end of the month before your Medicare start date. If you are not the sole subscriber, the policy should be kept in place but changed: you are Not Seeking Coverage – but you are still a household member, with your income included in determining your household’s eligibility for a Premium Tax Credit.

Our team can help you cancel or change your existing Individual Health Plan at the correct time.


Which is better? It depends.

  • If you are enrolled in an H.S.A. compatible health plan through your employer, you may elect to stay on that plan and defer Medicare Part A & B.
  • If you are enrolled in a non-H.S.A. compatible health plan through your employer, you may only enroll in Medicare Part A and defer Medicare Part B.
  • In most cases, Medicare coverage is better at a lower cost. In other instances where your employer’s plan would cost you less than Medicare, the employer would prefer to pay your Medicare premiums than the premiums under the employer group health plan. We recommend you approach your employer with a proposal to switch to Medicare, with them paying your Medicare premiums for as long as you are eligible for group health coverage. A win-win for everyone!

When can you change over to Medicare?

  • You have until eight months after leaving an employer group plan to join Medicare.
  • You have until eight months after stopping work to join Medicare (even if you are still on the group health plan)
  • Coverage under COBRA is NOT considered Creditable Coverage under your employer’s group health plan.

But to make the individual decision “Medicare or Employer Coverage” based on your circumstances, we recommend some research first:


  1. Are you required to drop the employer coverage? Or could you delay your Part B enrollment to stay on the employer plan?
  2. Is your employer's prescription drug coverage "Creditable Medicare Coverage"?
  3. What is the cost for each family member to be enrolled in the Employer's Plan? How much might you save if they were not enrolled in that plan?
  4. Would the employer contribute to the cost (via a buy-out) of your Medicare coverage if you continued to work but withdrew from the Employer's plan?
  5. Will the employer continue to contribute to your existing Health Savings Account if you stay on the Employer's Plan?


  1. Could you save money and/or get better coverage with Medicare?
  2. If you have family members under 65, what coverage, at what cost, is available in the Individual Market (coverme.gov)?


Do NOT enroll in Medicare Part A OR B at this time. Enrollment in Part A, while free, will disqualify you (or the employer) from making tax-deductible contributions to the Health Savings Account. 


Contact Social Security to Enroll in Part A only. You will refuse Part B now but take it later once the employer coverage ends. You can bill hospital claims to BOTH Medicare Part A AND your employer coverage.  How To Get Parts A/B. 


Contact Social Security to Enroll in Original Medicare Parts A & B within three months of turning 65. How To Get Parts A/B. 


Contact Social Security at least three months before your desired Part B start date and request a Part B Special Enrollment Period.  How To Get Part B Later

If you want Medicare when you first become eligible AND are currently collecting Social Security, wait for your Medicare card to come in the mail

If you are not collecting Social Security benefits but want Medicare at age 65

Enroll (at age 65) in Parts A & B, or Part A only

You are enrolling in a government program, so you have to contact the government to do it: Call the Social Security Administration at 1-800-772-1213 from 7am to 7pm, Monday through Friday or enroll online at https://www.ssa.gov/medicare

You can also apply using paper forms:

You can check the status of your Medicare application by clicking here.


If you are currently enrolled in Medicare Part A only and want to add Part B, you must:

Enroll (after age 65) in Part B


The most common Special Enrollment Period (SEP) is having coverage through your job or a spouse’s job and having that coverage end or stopping work (even if they offer to continue the health insurance for you).

* NOTE: COBRA is NOT Group Health coverage so don’t take COBRA for 18 months and then try to sign up for Medicare – you will miss this SEP and have to wait until the General Enrollment Period to sign up.


You should sign up for Medicare at the Social Security Administration as soon as possible but no more than 3 months prior to the intended start date for Medicare. To avoid the Late Enrollment Penalty, get your employer to provide proof of Creditable Coverage for the period since you turned 65 (or sign the Part B form).


If you have a PDF document (from your employer or your health plan) showing proof of insurance since turning 65, you can apply online here: https://secure.ssa.gov/mpboa/medicare-part-b-online-application/ and upload the document with your application


If you don’t have a PDF document showing proof of insurance since turning 65, download and complete the forms you need:


Find your Social Security office https://secure.ssa.gov/ICON/main.jsp and fax or mail them the completed forms directly to that office.




Valid SEP’s also include

  • Losing Medicaid (Mainecare)
  • Being impacted by a Natural Disaster or Emergency
  • Receiving inaccurate or misleading information from your health plan or employer
  • Being released from incarceration
  • Volunteer and serve in a foreign country
  • Have TRICARE
  • Experiencing other exceptional conditions.

If you are not sure if you qualify for a Special Enrollment Period, you can view the different types of SEPs here: https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start#SEP

To sign up for Medicare using any of these reasons, download the Application for Medicare Part A and B — Special Enrollment Period (Exceptional Conditions) (CMS-10797) here: https://www.cms.gov/files/document/application-medicare-part-part-b-special-enrollment-period-exceptional-conditions.pdf and submit to your local Social Security office. Find your Social Security office https://secure.ssa.gov/ICON/main.jsp and fax or mail them the completed form.


Some situations don’t qualify for a Special Enrollment Period:

  • Your COBRA coverage or retiree coverage ends.
  • You missed your 8-month window to sign up when you stopped working or lost job-based coverage.
  • You have or lose your Marketplace (ACA) coverage.
  • You have End-Stage Renal Disease (ESRD). Learn more about Medicare coverage for ESRD here: https://www.medicare.gov/basics/end-stage-renal-disease

If you don’t have a valid SEP, you must wait until the General Enrollment Period (Jan 1 to Mar 31) and you will pay an extra 10% (for the rest of your life) for EACH year you could have signed up for Part B but didn’t. Call Social Security at 1-800-772-1213 to discuss your options as soon as possible.


  • There is a monthly premium for Part B. In 2023 the base premium is $164.90 a month. If your income in the tax year two years prior (so, 2021) was more than $97,000 Single / $194,000 Married, your Part B premium would be higher. Check here: https://www.medicare.gov/your-medicare-costs/part-b-costs 
  • If you are collecting Social Security, the premium is deducted from your social security payment 

Otherwise, it is billed quarterly (although your first bill could be for as much as five months). Visit https://www.medicare.gov/your-medicare-costs/how-to-pay-part-a-part-b-premiums  to review your options for paying this bill monthly via your Medicare.gov account, via EFT, via bank payment service or through the mail.

One in five retired individuals qualifies for financial help with premiums and out-of-pocket costs.

  • The Medicare Savings Program can help pay for Premiums and Out of Pocket Medical Costs. This program is managed by the State of Maine
  • Extra Help with Prescription Drugs can help reduce your pharmacy costs. This program is managed by the U.S. Government. 
  • In 2022, you may qualify if you have up to $20k in yearly income ($28k for a married couple) AND up to $50k in cash or investments ($75k for a married couple).  
  • Apply online no more than three months before your Part B Start Date: https://www.ssa.gov/extrahelp and ask that your application be shared with the State of Maine. One application can be used for both MSP and Extra Help. 
  • If you need assistance, let us know.
  • For more information on Medicare costs, click here. 

Apply for Low-Income Financial Help


Once a Medicare card arrives (but no later than seven days before the expected Part B effective date), schedule an appointment here: https://calendly.com/wjwi. We’ll review:

  • Choosing between a Medicare Advantage plan (including prescription drug coverage) or a Medicare Supplement plan (with a standalone prescription drug plan).
  • With consideration given to provider network, medications needed, ratings & reputation of insurers, your health and financial status.
  • Medicare coverage takes effect the first of the month a person turns 65, so ideally, four weeks before that date, we’ve completed a review of needs and finalized an enrollment in a plan.
After you go through all the steps above, click here as it’s time to move on to Phase 2.

We do not offer every plan available in your area. Currently we represent 6 organizations that offer 46 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.