Does Enrolling In COBRA Protect You From Medicare Penalties?

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 Dear Toni:

I retired last June when I turned 66 from my employer of 20 years. I enrolled in COBRA which began July1 instead of enrolling in Medicare because I was told that COBRA protected me from the Medicare penalty for 18 months. My sister informed me about Medicare’s Special Enrollment Period in the Medicare & You Handbook which explained enrolling in Medicare Parts A and/or B when leaving your employer with health benefits.  The article stated that there is only an 8-month period that one can enroll in Medicare when leaving your employer.

My concern is that I may have missed my time to enroll in Medicare without receiving a penalty or not being able to enroll at all.  I read your weekly Medicare article and now I need Ms. Medicare to help me.  Toni, please explain what I need to do to be enrolled in Medicare the correct way.  Looking forward to what you have to say.

Thanks, Toni, Robert 

Hello Robert:

            Your situation is a little different than most American’s who are in the 8-month Special Enrollment Period because you have emailed me when you only have a few weeks to apply for Medicare.  Your 8-month period began July 1 and will end February 28.

            On page17 of the 2025 Medicare & You Handbook, it explains under “Special Enrollment Period” (SEP) the Medicare rule when you are no longer employed full-time with employer benefits.  America needs to understand that there is not an 18-month window for enrolling in Part B without a penalty when covered by COBRA. Waiting longer than 8-months will cause a penalty or not being able to enroll until Medicare’s next General Enrollment Period (GEP) which is from Jan. 1-Mar. 31.

Robert, you are lucky because you have both options Medicare’s SEP and GEP for enrolling in Medicare and they are:

• Option #1 Enrolling during Robert’s SEP to keep from not receiving a Medicare penalty: He reaches the 8^th month window in February and has very little time to file his Medicare with Social Security. To enroll in Medicare for a Special Enrollment Period (SEP) Robert should download form CMS-L564 (Request for Employment Information) and CMS- 40B (Application for Enrollment in Medicare-Part B) from gov/forms. It is vital that Robert personally take or email the CMS-L564 (Request for Employment Information) form to his employer’s human resources department to sign off on the form and attach it to CMS-40B (Application for Enrolling in Medicare Part B). Under #9 (Remarks) on the CMS-40B, write that the Medicare Part B should begin March 1.      File both forms with the local Social Security office as quickly as possible to have them filed before February 28. Take the CMS-L564 and CMS-40B to your local Social Security office. Let the Social Security agent know that your 8-month SEP window is closing, and Medicare needs to begin ASAP.
• Option #2 Medicare’s General Enrollment Period (GEP) will receive a Medicare penalty: Robert has 2 months left for Medicare GEP which is from Jan.1-Mar. 31each year for those who never enrolled in Medicare Parts A and B. The Medicare & You handbook under “General Enrollment Period” explains that when you enroll in Jan-Mar your Medicare Part B begins the first day of the following month. Wait past March 31 to enroll, your Medicare enrollment will be delayed until Jan.1, receiving a higher Part A and/or B late enrollment penalty (LEP). Robert, if you cannot enroll in Medicare’s SEP by February 28, then you can still enroll in Medicare during GEP with March being the last month with your Medicare beginning April 1 and will receive a Medicare penalty.

Always have Part B in place when leaving your job or losing your company benefits because the penalty goes back to the month you turn 65 or the month your Part A began.

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