When and How to Enroll in Medicare

If you’re approaching Medicare age, it’s important to know when you can sign up: the Initial Enrollment Period (IEP) at age 65 and the Special Enrollment Period (SEP) in the eight months after your current coverage ends.1 Missing these enrollment periods could leave you with gaps in your health insurance coverage and costly penalties.

How the Medicare Initial Enrollment Period works

The first opportunity to sign up for Medicare—at age 65—is known as the Initial Enrollment Period. The enrollment period for those signing up at age 65 is the three months preceding your 65th birthday, the month of your 65th birthday and the three months after your 65th birthday. To initiate Medicare coverage at the beginning of the month of your 65th birthday, you need to enroll within the three months prior to the month of your 65th birthday. If you sign up during the month of your birthday, your coverage will not begin until the first day of the following month. If you sign up during the three months after your birthday month, your coverage will start at the beginning of the month following the month you signed up during.2

If you have employer retiree coverage (including COBRA coverage), individual coverage or coverage through an employer of fewer than 20 employees, you may still need to act during your IEP in order to avoid any gaps in your coverage.3

If you miss your Medicare Initial Enrollment Period

If you miss your IEP for reasons other than a qualified event, such as your current employer providing insurance, there is a late enrollment penalty on your Medicare Part B premium as well as your Medicare Part D premium. For Medicare Part B, the penalty is 10% of your monthly premium for every full year that your enrollment is delayed past your Initial Enrollment Period.

In addition to the penalty, there may be a considerable delay before you have insurance coverage through Medicare because you will have to wait until the next General Enrollment Period, which is January 1 through March 31 every year.4 For those who sign up for Medicare during the General Enrollment Period, their coverage starts the month after they sign up.5 In some circumstances, this could mean a 65-year-old is without insurance coverage for up to a year and a half.

For Medicare Part D, the penalty is 1% of the standard Part D premium in effect for that year for every month the individual was without prescription drug coverage.

Both the Part B and Part D penalties follow you as long as you have Medicare and will change every year based on the Part B and Part D premiums of the individual.

Medicare Special Enrollment Period – your second chance to enroll

The second opportunity you have to sign up for Medicare is known as the Special Enrollment Period. While there are multiple ways to qualify for the SEP, a common one is the loss of health insurance from your employer or a spouse’s employer due to retirement or a severance/separation.

If you have no significant gaps in insurance coverage after age 65 and worked for an employer of 20 or more employees, you should qualify for a SEP. The SEP gives you eight months after the termination of the previous insurance coverage to sign up for Medicare without penalty.6

To ensure there is no coverage gap between the end of your previous insurance coverage and the start of Medicare, we suggest that you begin the process of enrolling in Medicare two to three months before your old coverage ends. If the eight-month period ends and you have not signed up for Medicare, you will be subject to similar penalties as those who missed their Initial Enrollment Period.

How to enroll in Medicare

If you are collecting Social Security at age 65, you will be automatically enrolled in Medicare Part A.7 Otherwise, you have the following ways to enroll:

  • Visit www.ssa.gov/medicare/sign-up. It is recommended that you review the following publication before enrolling online: www.ssa.gov/pubs/EN-05-10531.pdf 
  • Call Social Security at (800) 772-1213 between 8 a.m. and 7 p.m. Monday through Friday. Please be prepared for an extended wait to speak with someone. They may recommend that you schedule a telephone appointment with your local Social Security office. Record the names of the people you speak with and the date/time of your conversation.
  • Visit your local Social Security office. You can find the address here: https://secure.ssa.gov/ICON/main.jsp. To reduce wait time, it is recommended that you first call (800) 772-1213 to schedule an in-person appointment.

Enrolling in Medicare is a very specific process. It is important to establish a plan so you do not miss any of the critical dates or steps involved. For expert support, please reach out to your Wealth Advisor and start a conversation about Medicare.


1 https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
2 https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
3 https://www.medicare.gov/basics/get-started-with-medicare/medicare-basics/working-past-65
4 https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
5 https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
6 https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-can-i-sign-up-for-medicare
7 https://www.medicare.gov/basics/get-started-with-medicare/before-65


Bryan Smalley, CFP®

Bryan Smalley, CFP®

Wealth Advisor

Bryan is a Wealth Advisor in our Morristown, NJ, office. He is responsible for managing client relationships and coordinating all aspects of client service for the team. He currently serves on the firm’s Financial Planning Committee, providing research and input into such topics as Medicare and retirement planning. Bryan is an Ohio native (Go Bucks!) who has earned the CERTIFIED FINANCIAL PLANNER™ certificate along with a BA from the University of Toledo, an MA from Bowling Green State University and a certificate in Financial Planning from Boston University. Bryan, his wife, Liz, and their four children live in Flemington, NJ, where they enjoy exploring new places and spending time with family and friends.


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