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, Fla.

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. Americans need 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 Jan. 1-March 31.

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

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. He should then file both forms with the local Social Security office as quickly as possible to have them filed before Feb. 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 2 months left for the Medicare GEP, which is from Jan.1 to March 31 each year for those who never enrolled in Medicare Parts A and B. The Medicare & You handbook under “General Enrollment Period” explains that when someone enrolls during the January-March GEP, their Medicare Part B begins the first day of the following month. If they wait past March 31 to enroll, their 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 Feb. 28, then you can still enroll in Medicare during the GEP, with your Medicare beginning April 1, and you will receive a Medicare penalty.

Readers, 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.

Toni King is an author and columnist on Medicare and health insurance issues. She has spent nearly 30 years as a top sales leader in the field. For a Medicare checkup, call the Toni Says call center at (832) 519-8664 or email info@tonisays.com regarding your Medicare plans and options. Toni Says Medicare Survival Guide Advanced edition is available at www.tonisays.com.