The When and How of Medicare Supplement Enrollment


Many calls we receive start with an exasperated, newly minted Medicare eligible person who is struggling to understand the process.

What comes first? When should each step be completed?

And many more. Let's walk through the key steps and make it easy to understand.

When are you eligible for Medicare and Supplements

There are a few triggers but most people will be come eligible when they turn 65 or if they are 65 and older and lose group health insurance (through an employer). Those two triggers make up 90% of the enrollments and for good reason.

A new Part B election is the ultimate trigger in terms of your enrollment window.

If a person chooses not to enroll in a Medicare supplement during their open window, we can still try to enroll but it can be medically underwritten and/or more expensive for certain core benefits (such as Part D for medication).

Many people choose to just have Medicare without realizing the potential risk in doing so. The 20% coinsurance of Medicare is not capped which means you will have to pay that indefinitely.

If you only have Medicare and get a $50K bill, you could be on the hook for $10K. THAT's why you have a supplemental plan.

That's dangerous in light of cost of hospital care these days and especially at an age where larger bills are more likely.

Back to our timeline of Medicare enrollment

Step 1 - When to Enroll in Medicare Part A and B

The main window to enroll in a supplement plan is 3 months prior and 3 months after the triggering event in most situations.

For example, let's say I turn 65 on May 15th. I am officially eligible for Medicare (and a supplement) on May 1st. I have during the 3 months prior to May 1st and 3 months following May 1st to enroll. It's a total of 6 months.

The same rule would apply for losing group health insurance or the other triggers. Some people enroll in Part B while still with group health insurance but the loss of group coverage becomes the important trigger in that case.

Here are the Key Steps

Medicare Part A and B

First, make sure you are enrolled in Part A and B through Medicare. Most people can do this through  You'll receive a Medicare card with an effective date for both A and B. It's the effective date for Part B that is important.

If you are unable to process through the website, you can visit a Social Security office locally to enroll. Some people are unable if their relationship with Social Security was more complicated (did not earn income, etc).

People can "buy into" Medicare if they did not contribute via payroll (or spouse's payroll) during the course of their life.

Medicare Part A generally doesn't not have a cost. It's the part you've paid into all your life though payroll taxes.

Part B does have a monthly payment which depends on your income. You should be able to have this charge deducted from your Social Security check. The baseline Part B costs goes up a little each year and starts at about $105/month.

We recommend the Social Security deduction option so that you're coverage isn't jeopardized due to a move, mail issue, etc.

Key Tip: You need to "sign up" for Part B. It is not automatic. Part B monthly costs can increase if you have higher income.

TO DO: We recommend securing your Part A and B approximately two months prior to being eligible.

So that's the core Medicare enrollment. Let's look at the Supplement and Part D enrollment process.

Step 2 - Medicare Supplement Enrollment

Once your Medicare Part A and B is set up, we can apply for a Supplement or Advantage Plan. You can find more on how they differ here.



KEY TIP: We recommend submitting the application approximately 30 days prior to the 1st of the month that you're eligible for Medicare in.

Even though we can submit the enrollment anytime prior to the 1st that you want it effective, a good 30 days will provide enough time to get your ID cards, etc in case you need care..

You can quote all the major carriers for Supplements and Advantage Plans here.

We are happy to help you with the application and process and there is no charge for our services

More detail on plan options and best values

Step 3 - Part D Prescription Coverage




Part D follows the same rules as Medicare supplements above with two key differences:

  1. There is a monthly increasing penalty for not purchasing Part D coverage once eligible..e.
  2. You can change plans and carriers at the end of each year regardless of health.

KEY TIP You can get a "Place Holder" Part D plan to avoid the penalty but keep the cost as low as possible.

Since the penalty increases each MONTH, it's important to lock in a baseline coverage in case you need RX coverage at a later date.

Keep in mind that if you are on group health insurance which offers a qualified medication benefit, you will not accrue the penalty until you come off of the group plan.

For Part D, we provide a free service which is very advantageous to you.

Just send us your medications, doses, and # per month. We'll enter these anonymously into the Medicare system and generate a report which shows the best value in total costs (both monthly premium and d copays/out of pocket). This is the ONLY way to make sure you are saving on your RX coverage.

We can re-evaluate your options at the end of each year with Part D. For free!

Important: Some Advantage plans include the Part D already. We'll help you compare the plans base on your needs.

Those are the three key pieces:

  1. Part A and B through Medicareare
  2. Medicare Supplement or Advantage Plan
  3. Part D for medication (unless included in the Advantage Plan)

Timeline Reminders:

  1. Part A and B - 60 days prior to being eligible (example prior to the 1st of the month you turn 65)
  2. Medicare Supplement and Part D - 30 days prior to eligible date

Not so bad once it's all laid out neatly! Again, call us with any questions you have...especially regarding the plan differences. That's where things can get tricky.

You can get a quick lay of the Medicare supplement and Advantage landscape here but we're always available with friendly and patient listeners on the other line.

We'll make Medicare easy and we'll make the out of pocket costs lower. That's our job. Let us get to work. Call us at 800-320-6269 or email to 

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