How does Medicare’s fall enrollment affect me?

on Jun 12, 2025

I’m stressed about what I need to do to enroll in Medicare because I am working part-time with no benefits, only individual health insurance. I turn 65 in November and need my Medicare and Part D plan to begin Nov. 1.

How does Medicare’s fall enrollment period affect me, since I will be applying for Medicare this fall? How can I ensure I enroll in Medicare the right way? Thanks, Toni!

-- Devon from Cleveland

Hi Devon:

Don’t stress yourself about the Medicare Open Enrollment (OEP), aka Annual Enrollment Period (AEP), that begins Oct. 15, because you will be in your Medicare Initial Enrollment Period (IEP). This is Medicare’s special time for those who are just turning 65. During your IEP, you can pick the Medicare plan that best fits your medical and financial situation, whether it’s Original Medicare with a Medicare Supplement and a stand-alone Medicare Part D plan or Medicare Advantage plan with Part D included.

Next year’s OEP/AEP (in 2026 for 2027) is when you can make a change to either the Medicare Advantage Plan or Medicare Part D, depending on what you enroll in when you turn 65. This year’s OEP/AEP is not for you, Devon!

Medicare’s IEP is a 7-month window that begins 3 months before the month you turn 65, the month you turn 65, and 3 months after turning 65. If one waits past this 7-month period to enroll then Medicare’s Part B and D, penalties can begin. (My Medicare Survival Guide Advanced edition explains enrolling in Medicare in detail for those who are either turning 65 or who are past 65 and leaving an employer health plan, whether retiring or laid off.)

Medicare’s IEP timeline is:

-- If you enroll any time during the 3 months before turning 65, Medicare begins the first day of the month when you turn 65. (Devon turns 65 in November and can enroll in Medicare Parts A and B in August, September, or October (3 months prior) for a Nov. 1 effective date.)

-- If you enroll the month that you turn 65, then Medicare will begin on the 1st of next month. (If Devon enrolls in November, his Medicare will begin Dec. 1.)

-- If you enroll 1, 2, or 3 months after turning 65, then your Medicare will begin the 1st day of the month following enrollment.

Devon, since you are not receiving your Social Security check, you need to create a My Social Security Account through Social Security’s website at www.ssa.gov/medicare/sign-up and enroll yourself online. It is not commonly known that Social Security enrolls Americans in Medicare and that Medicare is not involved in this process.

Once your enrollment in Medicare is finalized on the Social Security website, then you will want to view your Benefit Verification Letter. At that time, you can verify your Medicare Part A and B starting dates with your new Medicare number and enroll in whatever Medicare health and prescription drug plans you would choose. Whether you pick a Medicare Supplement with a stand-alone Part D prescription drug plan or a Medicare Advantage HMO/PPO plan with prescription drug coverage, find a plan that best fits your medical and financial needs.

Good luck, Devon, with enrolling in Medicare the correct way!! Remember with Medicare it’s what you don’t know that WILL hurt you!

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Toni King is an author and columnist on Medicare and health insurance issues. She has spent nearly 30 years as a top sales leader in the field. If you have a Medicare question, email info@tonisays.com or call 832-519-8664. The “Medicare Survival Guide Advanced” edition and her new “Confused about Medicare” video series are available at www.tonisays.com.