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Dear Toni,

I’m stressed about what I need to do to enroll in Medicare because I am turning 65 in November and am not receiving my Social Security check since I am still working part-time with no employer benefits; I only have individual health insurance. I need my Medicare and Part D plan to begin Nov. 1.

I’m concerned about how Medicare’s fall enrollment time affects me since I will be applying for Medicare. How can I ensure I enroll in Medicare the right way? Thanks, Toni.

—Joshua from Kansas City, Kan.

Hi Joshua:

Don’t stress yourself about the Medicare Open Enrollment (OEP), also known as Medicare’s 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, that is, in the fall of 2027 for a start of Jan. 1, 2028, 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 in November. This year’s OEP/AEP is not for you!

Joshua, Medicare’s IEP is a seven-month window that spans the three months before the month you turn 65, the month you turn 65, and three months after turning 65. If one waits past this seven-month period to enroll, then Medicare’s Part B and D penalties will begin when that person finally enrolls. (The Toni Says 2026 Medicare Roadmap explains how to apply for 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 as follows:

—If you enroll any time during the three months before turning 65, Medicare begins the first day of the month when you turn 65. (Joshua turns 65 in November and can enroll in Medicare Parts A and B in August, September or October (three months prior) for both Medicare Parts A/B to begin with a Nov. 1 effective date.

—If you enroll the month you turn 65, then Medicare will begin on the first of next month. (If Joshua enrolls in November, his Medicare Part A will begin Nov. 1, and Medicare Part B will begin Dec. 1.)

—If you enroll one, two or three months after turning 65, then your Medicare Part A will begin the month you turn 65 and Medicare Part B will begin the first day of the month following enrollment. (If Joshua enrolls in December, his Medicare Part A is Nov. 1, and Part B is Jan. 1; if he enrolls in January then his Part A is Nov. 1 and Part B is Feb. 1; and the last month he can enroll when turning 65 is the month of February with his Medicare Part A beginning November 1 and Medicare Part B beginning March 1.) Confusing …? I know!

Because you are not receiving a Social Security check, Joshua, you will 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 America 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 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.

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Toni King is an author and columnist on Medicare, Social Security and long-term care 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. Sign up for the Toni Says newsletter at www.tonisays.com to keep up to date on Medicare changes.

©2026 Toni King. Distributed by Tribune Content Agency, LLC.

Copyright 2026 Toni King, Distributed by Counterpoint Media