ArcaMax

Dear Toni:

I retired from my employer in July when I turned 67 and enrolled in COBRA, which began August 1, instead of enrolling in Medicare. I was told that COBRA protected me from the Medicare penalty for 18 months.

My sister showed me a topic about Medicare’s Special Enrollment Period in her 2026 Medicare & You Handbook that explained how to enroll in Medicare when leaving your employer with health benefits. The handbook states that there is an eight-month (not 18-month period) to enroll in Medicare when leaving your employer. The handbook further states that COBRA doesn’t count as current employer coverage for the Special Enrollment Period. Now I am discovering that COBRA is not a Medicare plan at all.

Have I missed my time to enroll in Medicare without receiving a penalty? Am I not even able to enroll at all? Can you explain what I should do? Thanks, Toni.

—Eddie from Nashville, Tenn.

Hello, Eddie:

You are lucky that your sister showed you what is on pages 17-19 of the Medicare handbook because you are almost at the end of your eight-month Special Enrollment Period (SEP) to apply for Medicare. Your eight-month period began August 1 and will end March 31.

Page 17 of the handbook under “Special Enrollment Period” explains the Medicare rule when you are no longer employed full-time with employer health benefits. COBRA is generally an 18-month plan for those retiring and leaving employer benefits. Page 18 of the handbook notes that, whether or not you choose COBRA, you have eight months to sign up for Part B without a late enrollment penalty. Waiting longer than eight months to enroll in Medicare will cause a Medicare Part B penalty for as long as you have Part B.

Eddie, enroll before your eight-month SEP window is over on March 31. After April 1 your Medicare can be denied since you waited past your eight-month window, and you will have to wait until next year’s Medicare General Enrollment Period (GEP), which is from January 1 through March 31. The GEP time period is the only time one can enroll in Medicare when one has waited too long and will receive the Part B penalty.

Since you are past 65, there are Social Security forms that your employer must provide stating that you have been enrolled in employer benefits since turning 65.

Here are the steps to take to enroll in Medicare the right way.

—Download two forms: CMS-L564 (Request for Employment Information) and CMS-40B (Application for Enrollment in Medicare Part B) from SSA.gov/forms. It is vital that Eddie email or take the CMS-L564 form to his employer’s human resources department to sign off on. Then attach the signed CMS-L564 to CMS-40B, which is filled out and states that Eddie wants his Medicare Part B to begin April 1.

—Before filing both forms with the local Social Security office, remember to write “Special Enrollment Period” at the top of each form so the agent finalizing the enrollment knows this filing is during a SEP time and not the Medicare General Enrollment Period (GEP).

—File forms with the local Social Security office before April 1 or before the eight-month window will expire. Make copies of every document given and received from the Social Security office and ask for the name of the agent you give the forms to.

Both of Toni’s books and her new “Confused about Medicare” online course and Toni Says Medicare Roadmap are available at www.tonisays.com.

_____

_____

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