UNITED STATES—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 8-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? I need Miss Medicare’s help! Thanks, Toni. -Eddie from Nashville, Tenn.
Hello Eddie: You are lucky that your sister showed you what is on page 17-19 of the Medicare handbook because you are almost at the end of your 8-month Special Enrollment Period (SEP) to apply for Medicare. Your 8-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 8 months to sign up for Part B without a late enrollment penalty. Waiting longer than 8 months will cause a Medicare Part B penalty for as long as you have Part B.
Eddie, enroll before your 8-month SEP window is over on March 31. After April 1, your Medicare can be denied since you waited past your 8-month window, and you will have to wait until next year’s Medicare General Enrollment Period (GEP) which is from January1-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 “infamous” Part B penalty.
Since you are past 65, then there are Social Security forms that your employer must provide stating that you have been enrolled in employer benefits since turning 65.
Below is the information on how to enroll in Medicare past 65 and working with employer health benefits to not receive a Part B penalty:
- Download 2 forms: CMS-L564 (Request for Employment Information) and CMS- 40B (Application for Enrollment in Medicare-Part B) from gov/forms. It is vital that Eddie email or take the CMS-L564 form (Request for Employment Information) to his employer’s human resources department to sign off on the form. Then attach the signed CMS-L564 to CMS- 40B (Application for Enrolling in Medicare Part B) 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”( SEP) at the top of each form for the Social Security agent finalizing the enrollment knows this filing is during a SEP time and not Medicare General Enrollment Period (GEP) to not receive a Part B penalty.
- File forms with the local SS office before April1 or before the 8-month window will expire. (Eddie’s SEP ends March31.) Make copies of every document given and received from the SS office and ask for the name of the SS agent you give the forms to.
Don’t forget!! With Medicare…What you don’t know WILL hurt you!! For more Medicare information, email info@tonisays.com or call 832-519-8664. Both of Toni’s books and her new “Confused about Medicare” online course and Toni Says Medicare Roadmap are available at www.tonisays.com.
