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Does enrollment in COBRA protect you from Medicare penalties?

Updated February 20, 2025 - 12:57 pm

Dear Toni: I retired from my employer of 20 years in 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 for signing up for Medicare Parts A and B. The “Medicare & You” handbook states that there is only an eight-month period when one can enroll when leaving employer benefits.

My concern is that I may have missed my time to enroll without receiving a penalty or not be able to enroll at all. Please explain what I need to do. — Robert, Tampa, Fla.

Dear Robert: Your situation is a little different from most Americans who are in the special enrollment period. Your eight-month period began July 1 and will end Feb. 28.

People need to understand that there is not an 18-month window for enrolling in Part B without a penalty when covered by COBRA health insurance. Waiting longer than eight months means you’ll pay a penalty or not be able to enroll until Medicare’s next general enrollment period (Jan. 1-March 31).

Robert, you have both options available: Medicare’s special enrollment period and general enrollment period.

Option 1: Enrolling during the special enrollment period to avoid a Medicare penalty.

Robert has very little time to file his Medicare with Social Security before the end of his eight-month window. To enroll during his special enrollment period, Robert should download forms CMS-L564 (Request for Employment Information) and CMS-40B (Application for Enrollment in Medicare-Part B) from ssa.gov.

He must have his former employer’s human resources department sign his CMS-L564 form and attach it to CMS-40B. Under “Remarks” on the CMS-40B, Robert will write that his Medicare Part B should begin March 1. He should submit both forms to his local Social Security office as quickly as possible to have them filed before Feb. 28.

Option 2: Enrolling during Medicare’s general enrollment period.

If Robert enrolls under this period, he will receive a Medicare penalty. When enrolling within this window, your Medicare Part B will begin the first day of the following month. If you wait past March 31, your Medicare enrollment will be delayed until Jan. 1, resulting in a higher late-enrollment penalty.

Readers, always have Part B in place when losing company benefits. Otherwise, the penalty will go back to the month you turned 65 or the month your Part A began.

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.

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