Medicare Enrollment: A Quick Guide for “First Timers”

By Judson Meinhart, CFP®, BFA™, CTS

Director of Financial Planning, Wealth Manager & Principal

October 13, 2023

Is this your first time enrolling in Medicare and wondering what to do?

Do you know if you qualify or when you need to enroll if you do?

There is no one-size-fits-all path to Medicare enrollment and there are a number of different directions you might take depending on your circumstances, such as your age, employment status, or whether you receive Social Security or Railroad Retirement Benefits.[1] This guide will help you with the most basic elements, general plan information and when to enroll.

What is Medicare anyway?

Medicare is a federally funded and operated insurance program primarily designed to help the U.S. population of senior citizens. Over 64 million Americans are currently enrolled.[2] Before you enroll yourself, it’s important to understand when you’re eligible for Medicare coverage and the benefits and costs of each plan.

Let’s start by looking at the various Medicare plans. Here is brief description of each plan, in simple terms:

Should I enroll?

Once you have thoroughly reviewed the plans and have a firm understanding of cost and coverage, you still need to ascertain when you will need to enroll and what coverage you will need based on your life circumstances. Here are just a few points to consider when asking yourself whether you need to enroll:

  • If you have already claimed Social Security, have been receiving Social Security disability benefits for at least 24 months prior to eligibility, or if you receive Railroad Benefits, you will automatically be enrolled in Part A and B when you turn age 65. Your Medicare card will arrive 3 months prior to your 65th birthday.
  • If you are not working or have no employer-sponsored health insurance, you should enroll during the Initial Enrollment Period (IEP) which is explained below.
  • If you are still working and you do have employer sponsored group health insurance, it gets a little tricky:
    • If your company has less than 20 employees, in most cases you must still enroll during the Initial Enrollment Period (IEP).
    • If your company has more than 20 employees, you’ll be eligible to enroll in Part A, but you will most likely need to enroll in Part B during a Special Enrollment Period (SEP) after employer coverage ends.

What is an enrollment period and why is it important?

Like much in life, timing is everything. When you are approaching your eligibility time and have determined the right plan for you, make certain you enroll at the right time. Not doing so could make coverage more costly to you.

Remember if you are receiving Social Security, Social Security disability benefits, or Railroad Retirement benefits you are automatically enrolled when the time comes.

For everyone else, you need to pay attention to enrollment periods.

Initial Enrollment Period (IEP)

The Initial Enrollment Period (IEP) is the 7-month window of time surrounding the month of your 65th birthday.  For example, if your 65th birthday is in July, your IEP will span from April until October.

But don’t wait until the last minute. To get coverage when you’re first eligible, you must enroll the month before you turn 65 to ensure you’re covered in the month you celebrate your milestone birthday.

Special Enrollment Period (SEP)

The Special Enrollment Period (SEP) applies to those over the age of 65, who are still covered by group health insurance through an employer in a company with more than 20 employees and who:

  • become unemployed and/or
  • no longer have group insurance coverage available to them.

The SEP enrollment window begins the month after you stop working or your group health coverage ends and lasts for 8 months.

The sooner you enroll the sooner your coverage begins (one month following your enrollment date).

Late Enrollment and Penalties

It is critical you sign up for Medicare when you are eligible, based on your life circumstances as we have discussed. If not, you can face some unnecessary and costly penalties in the form of late fees.[3] These fees are added into your premium and go up in cost the longer you wait to enroll. For example:

  • If you do not qualify for premium-free Part A and you do not enroll during your IEP, your premium may go up 10% more than typical and you will pay that amount for twice the number of years you could have been covered.
  • If you don’t enroll in Part B when you’re first eligible, your premium may go up 10% for each year you could have been covered.
  • If you don’t enroll in Part D or another prescription drug coverage within three months of the expiration of your IEP or SEP, you will pay an additional 1% of the national base beneficiary premium for each month you went without coverage.
Plan Your IEP or SEP ended in January 2023… … but you didn’t enroll until March 2024 Your penalty is … Penalty totals
Part A Premium $506/month* $556.6/month 10% extra for 2 years (double the amount of time without coverage) $1214.40
Part B Premium $164.90/month $181.40/month 10% extra for one 12-month period without coverage $198
Part D Premium $33.37/month $37.04/month 11% extra for 11 months without coverage $44.04

*In 2023, Plan A can cost up to $506/month.


Bottomline, when you are eligible for Medicare, based on your personal circumstance, it doesn’t pay to delay enrollment.

Contact an Experienced Wealth Management Advisor Near You

Do you have questions about your Medicare eligibility or other retirement planning matters? Schedule a call with one of our knowledgeable advisors today. We are proudly a fee-only, independently-owned financial planning firm that acts as a fiduciary for our clients. We have built our organization to put our customers’ interests first, as evidenced by our fee-only fee structure and fiduciary responsibility.

If you’re interested in our services, please contact us. If you would like to learn more about financial planning, wealth management, and finding a financial advisor, please visit other areas of our education section.

Contact us

"*" indicates required fields

Choose the one that fits you best:*
Approximately how much are you looking to have managed?*
(Modera has a $1M minimum.)

By sending this message, you agree that Modera will use the personal information you disclose to have an adviser contact you and/or you agree to opt-in to receive marketing communications from us.

This field is for validation purposes and should be left unchanged.

Modera Wealth Management, LLC (“Modera”) is an SEC registered investment adviser. SEC registration does not imply any level of skill or training. Modera may only transact business in those states in which it is notice filed or qualifies for an exemption or exclusion from notice filing requirements. For information pertaining to Modera’s registration status, its fees and services please contact Modera or refer to the Investment Adviser Public Disclosure Web site ( for a copy of our Disclosure Brochure which appears as Part 2A of Form ADV. Please read the Disclosure Brochure carefully before you invest or send money.

This article is limited to the dissemination of general information about Modera’s investment advisory and financial planning services that is not suitable for everyone. Nothing herein should be interpreted or construed as investment advice nor as legal, tax or accounting advice nor as personalized financial planning, tax planning or wealth management advice. For legal, tax and accounting-related matters, we recommend you seek the advice of a qualified attorney or accountant. This article is not a substitute for personalized investment or financial planning from Modera. There is no guarantee that the views and opinions expressed herein will come to pass, and the information herein should not be considered a solicitation to engage in a particular investment or financial planning strategy. The statements and opinions expressed in this article are subject to change without notice based on changes in the law and other conditions.

Investing in the markets involves gains and losses and may not be suitable for all investors. Information herein is subject to change without notice and should not be considered a solicitation to buy or sell any security or to engage in a particular investment or financial planning strategy. Individual client asset allocations and investment strategies differ based on varying degrees of diversification and other factors. Diversification does not guarantee a profit or guarantee against a loss.

Certified Financial Planner Board of Standards, Inc. (CFP Board) owns the certification marks CFP®, CERTIFIED FINANCIAL PLANNER™, and CFP® (with plaque design) in the United States, which it authorizes use of by individuals who successfully complete CFP Board’s initial and ongoing certification requirements.