Turning 65 and Still Employed, Will Medicare Kick in Automatically?

Dear Toni,
I’m turning 65 this January and have some questions about enrolling in Medicare. I’m still working, so I need clarity on a few points:
- Will my Medicare start automatically in January, even though I’m still working?
- If I retire at 67, do I stay on COBRA or enroll in a Medicare plan?
- What happens if I get another job?
I’ve heard different opinions from friends and telemarketers, which is confusing. Could you please explain what I should do? I’m sure others have similar questions!
Signed,
Confused in Corpus Christi
Does Medicare Start Automatically When You Turn 65?

You’re wise to ask these questions now! Properly enrolling in Medicare will help you avoid late enrollment penalties, which can be costly over time. Let’s break down your questions one by one.
Is Medicare enrollment automatic?
Medicare enrollment is automatic ONLY if you’re already receiving Social Security benefits before you turn 65. If you aren’t, you’ll need to apply online at ssa.gov/medicare/sign-up, especially if you’re not working full-time with employer benefits or want Medicare as your health coverage.
For those leaving an employer after age 65, your employer must complete Medicare form CMS-L564 (Request for Employment Information). Meanwhile, you’ll fill out CMS-40B (Application for Enrollment in Medicare Part B). Write “Special Enrollment Period” at the top to denote enrolling after age 65. Submit both forms to your local Social Security office to start your Medicare coverage. It’s that simple!
COBRA vs. Medicare

Should you enroll in Medicare if offered COBRA?
Yes, you should enroll in Medicare. While you might need COBRA to cover a spouse or dependent child, Medicare should be your primary coverage once you’re 65 or older and not working full-time with company benefits. You should enroll in Medicare Parts A and B.
Consider which option best suits your needs:
- A Medicare Supplement that pairs with “Original Medicare” and a stand-alone Medicare Part D plan
- OR a Medicare Advantage plan that includes Part D coverage.
Many COBRA plans allow retirees who are enrolled in Medicare Parts A and B to leave the COBRA plan while their family remains covered.
Returning to Work: Re-Enrollment Concerns

What if you become unemployed or retire, enroll in Medicare, and then return to full-time work?
If your new employer offers health insurance, you can disenroll from Medicare Part B. Simply contact Medicare at 1-800-633-4227 to request a form to delay your Part B. You won’t need it since you’re now covered by employer benefits.
Fortunately, you can re-enroll in Medicare Part B without penalties when you finally retire. This requires your current employer to sign form CMS-L564, which you’ll file with the CMS-40B form to reapply for Medicare Part B through Social Security.
Seek Reliable Medicare Advice

Following advice from friends who aren’t familiar with Medicare’s specific rules can jeopardize your coverage. Always research the facts. With Medicare, what you don’t know can hurt you!
❓❓Have More Questions? I’m Here to Help!❓❓
If you or anyone else has more questions, you’re welcome to call my Medicare Hotline at 832-519-8664. You can also visit my website, ToniSays.com, or email me at [email protected]. I’ve even written a book, The Medicare Survival Guide Advanced Edition, which breaks down everything you need to know about Medicare in plain English.
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Originally published October 24, 2024









