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Tuesday, November 3, 2026Nov 3

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Medicare rules confuse HR manager

Hello Toni,

I am a human resources manager for an oil and gas company and have a question about an employee who is turning 65. His situation is a little different because next month he will begin receiving chemotherapy for cancer. I’m not sure how to advise him, because technically, he is working full time. He has five months of pay from unused vacation time that he can use while recuperating, which will keep his status as a full-time employee.

Our firm has over 100 employees, and I have been told there are rules based on company size. How can I make sure I have the correct answer to my questions on behalf of the employees of our company?

— Katie, Tampa, Florida


Hi Katie,

Your employee with cancer is approaching his Medicare initial enrollment period, which begins three months before his 65th birthday month and ends three months after his 65th birthday month. Many Americans do not enroll in Medicare when turning 65 because they (or their spouse) are “still working” for an employer with over 20 employees and have employer group health insurance, such as your company. This rule can protect your still-working, full-time employee with health issues.

Now, readers, let us talk about who will pay your claim first. This depends on how many employees are on your company’s group health plan.

— If you are 65 or older and there are 20 or more employees where you (or your working spouse) receive benefits, the group health insurance pays first. (Please verify there are 20 or more employees enrolled in the employer group health plan). It may be to your advantage to delay enrolling in Medicare without receiving a Part B penalty.

— If there are fewer than 20 employees where you or your spouse work and receive benefits, generally Medicare pays first. You or your HR department should verify with the insurance carrier as to how the current health insurance plan coordinates with Medicare to determine whether you should enroll in Medicare Parts A and/or B or should delay enrollment in one or both.

Katie, below are a few items that can make your HR role job easier:

— Verify your employees’ options by calling your company’s health insurance plan to discover how the plan coordinates with Medicare.

— Understand that it may be to an employee’s advantage to delay Part B enrollment. See the “Medicare & You” handbook under “I have other health coverage. Should I Get Part B?” or Chapter 1 of my book “Medicare Survival Guide Advanced” edition for more clarification.

— Let employees who are past age 65 know they should contact their local Social Security office immediately to enroll in Medicare if their work status changes from full time to part time, laid off or retired. They will need to file the Social Security forms to avoid the infamous Medicare Part B penalty. They will be eligible for a special enrollment period and should enroll in retiree benefits such as a Medicare supplement or Medicare Advantage plan. It is important to remember Cobra and retiree insurance are not considered current employer insurance, so do not delay in enrolling in Medicare Parts B and D (Medicare’s prescription drug plan).

Readers, there are specific Medicare rules regarding leaving employer benefits after turning 65. Learning when and how to change Medicare plans and which Medicare Part D prescription drug plans best fit one’s health situation is especially vital for an employee such as Katie’s, who has cancer issues.

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. If you have a Medicare question, email info@tonisays.com or call 832-519-8664. Toni’s new book, “Maze of Medicare,” is available at tonisays.com. “Maze of Medicare” is the first explanatory book that includes scripture and positive quotes to help relieve the stress and anxiety over transitioning to Medicare.