UNITED STATES—Dear Toni: I retired from my employer of 20 years last June when I turned 66, I enrolled in COBRA, which began July 1, 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. — Robert from Tampa, FL.

Hello Robert: Your situation is a little different from most Americans 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 without penalty. Your 8-month period began July 1 and will end February 28.

On page 17 of the 2025 Medicare & You Handbook under “Special Enrollment Period” (SEP), it explains 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 means you’ll pay a penalty or not be able to enroll until Medicare’s next General Enrollment Period (GEP) which is from Jan. 1-March 31.

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

  • Option 1: Enrolling during the SEP to avoid receiving a Medicare penalty. Robert reaches the 8th 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 SSA.gov/forms. It is vital that Robert personally take or email the CMS-L564 (Request for Employment Information) form to his former employer’s human resources department to sign the form and attach it to CMS-40B (Application for Enrolling in Medicare Part B). Under #9 (Remarks) on the CMS-40B, Robert should 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. He should take the CMS-L564 and CMS-40B to his local Social Security office and let the Social Security agent know that his 8-month SEP window is closing, and his Medicare needs to begin ASAP.
  • Option 2: Enrolling during Medicare’s General Enrollment Period (GEP). If Robert enrolls under his GEP he will receive a Medicare penalty. He has two months left for the Medicare GEP, which is from Jan.1-March 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 during January-March GEP, your Medicare Part B begins the first day of the following month. If you 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 the GEP, with your Medicare beginning April 1 and you will receive a Medicare penalty.

Remember, 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.

For Medicare help, call the Toni Says Medicare call center at 832-519-8664 or email info@tonisays.com.