Toni Says: Does enrolling in COBRA cause a Medicare nightmare?

Waiting longer than 8 months will cause a Medicare penalty, whether or not you choose COBRA.
Waiting longer than 8 months will cause a Medicare penalty, whether or not you choose COBRA.
Waiting longer than 8 months will cause a Medicare penalty, whether or not you choose COBRA. [ Shutterstock ]
Published Jan. 31

Dear Toni:

I lost my job in October 2021 due to COVID layoffs in the oil industry, and my wife and I are now enrolling in Medicare Part B since the company-paid 18 months of COBRA is almost over. Now I am finding out that there will be a penalty for not enrolling when we should have!

I have never received a Medicare & You handbook to know how or when to enroll in Medicare properly. I was unaware of the Medicare rules until I began reading the Toni Says Medicare column in my local newspaper.

We are now 70 years old and the Part B penalty for us is each 50% since it has been 5 years since we were 65 and enrolled in Medicare Part A. Please inform your readers how important it is to enroll at the correct time when covered by COBRA.

- Robert from Charleston, S.C.

Toni King
Toni King [ Courtesy of Toni King ]

Hello Robert:

There is not an 18-month window to enroll in Medicare Part B when covered by COBRA. The window to enroll in Part B is 8 months under a “Special Enrollment Window” when you are no longer employed full-time with company benefits. Waiting longer than 8 months will cause a Medicare penalty, whether or not you choose COBRA.

As you know, these penalties can be extremely costly, and that penalty will last until you pass away or are no longer on Medicare.

ALWAYS, be sure that your Part B begins the day you lose your company benefits or the day your COBRA plan starts. Chapter 1 of the Medicare Survival Guide Advanced edition explains the rules of enrolling in Medicare the right way with a sub-chapter discussing enrolling in COBRA.

Many Americans who chose COBRA then enroll in their Part B with a big surprise like you have, Robert. They find they are penalized because they could have had Part B but did not. The penalty goes all the way back to the day he/she turned 65 or the day Medicare Part A began.

I have a 79-year-old client who has always been on his wife’s company health plan. He never enrolled in Medicare Part B because his wife was the “working spouse.” But she lost her job. She was 62, and because she had health issues and the cost of COBRA was less than an individual health plan, she enrolled herself and her 79-year-old husband in COBRA. When the COBRA ended 18 months later, they went to Social Security to enroll him in Part B and were shocked! His premium for Part B was not $164.90 for 2023. It was $164.90 plus a $230.86 penalty for late enrollment for a total of $395.76 per month. This was a 140% penalty: 79 minus 65 equals 14 years x 10%. He will have to pay this penalty each month for the rest of his Medicare life. You say, “Toni, how can this be?” And here is the answer: He did not enroll in “Part B” at the right time or the correct way.

Follow trends affecting the local economy

Follow trends affecting the local economy

Subscribe to our free Business by the Bay newsletter

We’ll break down the latest business and consumer news and insights you need to know every Wednesday.

You’re all signed up!

Want more of our free, weekly newsletters in your inbox? Let’s get started.

Explore all your options

So always have your Medicare Part B in place when leaving your job or losing your company benefits because the penalty goes back to the day you turn 65 and enrolled in Medicare Part A or the month your Part A began. There might not be a second chance! We at Toni Says advise clients not to wait out the whole 8-month Special Enrollment Window to sign up.

“Confused about Medicare” Zooms are back for 2023! Find the link at to register for the session on Thursday, February 9, from 4-6 p.m. Central time.

• • •

Toni King is an author and columnist on Medicare and health insurance issues. She spent more than 27 years as a top sales leader in the field. For a Medicare checkup, email: or call 832-519-8664. You can now visit to listen to her Medicare Moments podcasts and get other information for boomers/seniors.