Are You Working Past 65? Discover How Employer Coverage Affects Medicare Enrollment
Published: October 1, 2025 | Last updated: October 23, 2026
In short: If you're still working at 65 and covered by a group health plan from an employer with 20 or more employees, you can usually delay Part B without a penalty. Many people still take premium-free Part A. If your employer has fewer than 20 employees, Medicare usually pays first, so you should enroll in Parts A and B when you're first eligible. When your job or coverage ends, you have 8 months to sign up for Part B without a penalty.
Are you or your spouse planning to continue working past age 65 and will still be covered by an employer health plan? You might be wondering how Medicare fits into the picture, and we’re here to help you understand how to make the right decision for you and your family.
What You Need to Know:
Employer with More Than 20 Employees: If you’re working for a company with 20 or more employees, your employer’s plan is your primary coverage. You can choose to delay enrolling in Medicare Part B without penalties, but enrolling in Part A is often a good idea, as it’s typically premium-free.
Employer with Fewer Than 20 Employees: If your company has fewer than 20 employees, Medicare becomes your primary coverage, and you’ll need to enroll in both Part A and Part B when you’re first eligible.
Forms to Complete: When you decide to enroll in Medicare, there are certain forms to complete, especially if you’re delaying Part B or transitioning from an employer plan to Medicare.
What Should I Do Before I Turn 65 If I'm Still Working?
If you or your spouse are 65 or older and still covered by an employer plan, a few simple steps will help you avoid gaps and penalties:
1. Talk to your HR or benefits administrator. Ask how your employer coverage works with Medicare, and whether it pays first or second.
2. Check your employer's size. If your employer has 20 or more employees, you can usually keep your current coverage. It may make sense to enroll in premium-free Part A and delay Part B. If your employer has fewer than 20 employees, Original Medicare pays first, so apply about 3 months before your 65th birthday.
3. Contact Social Security if you need to enroll. If you don't already get Social Security benefits, reach out about 3 months before you turn 65: call 1-800-772-1213 (TTY 1-800-325-0778) or visit socialsecurity.gov.
4. Review your options with a local agent. We'll compare your employer plan with your Medicare options and help you decide what makes sense for you.
When Do I Sign Up for Part B After I Retire?
If you worked past 65 and had group coverage through your current employer (or your spouse's), you get a Special Enrollment Period. You can sign up for Medicare while you're still on the group plan, or during the 8 months after your employment or group coverage ends, whichever comes first, without a late penalty.
Don't wait until the end of that window. Signing up a month or two before your employer coverage ends helps you avoid a gap. Your 6-month Medigap Open Enrollment Period also starts when your Part B begins. That's the best time to buy a Medicare Supplement plan, because insurers can't turn you down for health reasons.
For a full walk-through of enrollment, download our free Medicare Guidebook.
Should I Sign Up for Medicare If I'm Still Working?
Navigating Medicare while working can be tricky. It’s important to understand how your employer coverage works with Medicare so you don’t miss key enrollment periods or face penalties later on.
Call us at (803) 256-2067 (TTY: 711) to speak with one of our Medicare experts. We’ll help you make the best decision for your wants and needs. We have offices in Columbia, Greenville, and Myrtle Beach! We can help you in person or over the phone.
Be sure to subscribe to our YouTube channel for more easy-to-understand Medicare tips! Watch the video here: https://www.youtube.com/watch?v=m1Tjl4Pbz78
Frequently Asked Questions
Can I delay Medicare if I have insurance through my job?
Usually, yes, if your employer has 20 or more employees and you have coverage based on current employment. Check with your employer's benefits team and an agent before you decide.What if I'm covered by my spouse's employer plan?
The same rules generally apply. The coverage must be based on your spouse's current employment, and the employer's size still matters.
Can I keep contributing to my HSA after I enroll in Medicare?
No. Once you enroll in any part of Medicare, including Part A, you can no longer contribute to a Health Savings Account. Part A can be backdated up to 6 months, so plan to stop contributions ahead of time.
Does COBRA or retiree coverage let me delay Part B?
No. COBRA and retiree coverage aren't based on current employment, so delaying Part B could lead to a late enrollment penalty.
What forms do I need when I leave my employer plan?
You'll typically need form CMS-40B (Application for Enrollment in Part B) and form CMS-L564 (Request for Employment Information), completed by your employer. We can help you fill them out.
Does it cost anything to get help?
No. Lourie Life & Health's service is at no cost to you.
Planning to work past 65 or getting ready to retire? Call a local South Carolina Medicare agent at (803) 256-2067 (TTY 711). We'll review your employer coverage and help you time your Medicare enrollment.
Want the full picture? Download our free Medicare Guidebook.