Dear Toni: I retired in July when I turned 67 and enrolled in COBRA, which began Aug. 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.
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? — Eddie, Nashville, Tennessee
Dear Eddie: You are lucky that your sister showed you her Medicare handbook, because you are almost at the end of your eight-month special enrollment period, which began Aug. 1.
Under “Special Enrollment Period,” the handbook explains the Medicare rule that applies 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. 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 will result in a Medicare penalty for as long as you have Part B.
Be sure to enroll by March 31, Eddie. Come April 1, your Medicare coverage can be denied since you waited past your eight-month window, and you would have to wait until next year’s general enrollment period (Jan. 1-March 31).
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 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. Email or take the CMS-L564 form to your employer’s human resources department to sign off on. Then attach the signed CMS-L564 to CMS-40B, which will state that you want your Medicare Part B to begin April 1.
Mark the forms: Before filing both forms with your local Social Security office, remember to write “special enrollment period” at the top so the agent finalizing the enrollment knows this filing is during a special enrollment window and not the general enrollment period.
Don’t miss the deadline: File your forms with the local Social Security office before the eight-month window expires. Make copies of every document given to and received from the Social Security office and ask for the name of the agent who helps you.
Toni King is an author and columnist on Medicare and health insurance issues. If you have a Medicare question, email info@tonisays.com or call 832-519-8664.
