WORKING PAST 65
Still Working at 65?
You May Be Able to Delay Medicare.
If you have health coverage through your current employer, you may be able to delay Part B without a penalty. The rules depend on your coverage and employer size, so it’s important to understand your options before making a decision.
No cost for our help. No pressure. Just clear Medicare guidance.
IT ALL STARTS WITH ONE KEY QUESTION
How Many Employees Does
Your Employer Have?
The size of your employer can affect whether you need to enroll in Medicare at 65.
20+ Employees
You can usually delay Part B.
If your current employer has 20 or more employees and your coverage is based on current employment, the employer health plan generally pays first and Medicare pays second.
Keep your current employer coverage
Possibily delay Part B without a late-enrollment penalty
Review your Medicare options yearly.
Use a Special Enrollment Period when your employment or qualifying coverage ends
Fewer than 20 Employees
You will generally need to enroll.
If your current employer has fewer than 20 employees, Medicare generally becomes the primary payer when you turn 65. Delaying Medicare could leave you with coverage gaps or unpaid medical bills and possibly late enrollment penalties.
Enroll in Medicare Parts A & B at 65
Consider your prescription drug coverage
Review your options for supplemental Medicare coverage
Determine whether keeping your employer plan makes sense
OTHER IMPORTANT CONSIDERATIONS
There's More to Consider
Your situation is unique. Here are a few other factors that can affect your Medicare choices when you're still working at 65.
Current vs. Retiree Coverage
The rules can be very different for active employer coverage and retiree coverage. Coverage based on current employment may allow you to delay Medicare, while retiree coverage generally does not allow you to delay Part B without potential penalties.
Health Savings Account (HSA)
Enrolling in Medicare affects your ability to contribute to an HSA. Timing matters because Part A can sometimes be retroactive when you enroll after age 65. Once Medicare coverage begins, you can no longer contribute to an HSA, although you can still use the money already in your account.
Spouse Coverage
Coverage through your spouse’s current employer may allow you to delay Medicare. The rules depend on whether your spouse is actively working, the size of the employer, and the type of coverage you have.
Special Enrollment Period (SEP)
When employment or qualifying employer coverage ends, you may qualify for a Special Enrollment Period to enroll in Part B without a late-enrollment penalty. Understanding when your enrollment window begins can help you avoid gaps in coverage.
When You Retire
You generally have an 8-month Special Enrollment Period for Part B after employment or qualifying employer coverage ends. However, other Medicare deadlines, including prescription drug coverage, can be shorter. Planning ahead can help you avoid coverage gaps and penalties.
Prescription Drug Coverage
Even if you delay Part B, you still need to understand whether your employer prescription coverage is considered creditable coverage. Going without Medicare Part D or other creditable drug coverage for too long can result in a late-enrollment penalty.
FREQUENTLY ASKED QUESTIONS
Working Past 65 and Medicare
Can I keep my employer health insurance and delay Part B?
Possibly. If you or your spouse are actively working and you’re covered by a current employer’s group health plan, you may be able to delay Part B without a late-enrollment penalty.
Employer size and the type of coverage matter. With 20 or more employees, the employer plan generally pays first. With fewer than 20 employees, Medicare generally pays first, so enrolling in Medicare at 65 may be necessary to avoid coverage gaps.
Does it matter if I’m still working but covered under my spouse’s plan?
Yes, but coverage through your spouse’s current employment may allow you to delay Part B just as coverage through your own employer can.
The important questions are whether your spouse is actively working, whether the coverage is based on that current employment, and the size of the employer. COBRA and retiree coverage are different and generally do not protect you from a Part B late-enrollment penalty.
Can I contribute to an HSA if I enroll in Medicare?
No. Once you’re enrolled in Medicare, you can no longer contribute to a Health Savings Account, although you can continue using money already in the account for qualified medical expenses.
Timing is especially important because Medicare Part A can sometimes be retroactive for up to six months when you enroll after age 65. If you're contributing to an HSA, we should review your Medicare enrollment timing before you apply.
What forms do I need when I’m ready to enroll?
If you delayed Part B because you had qualifying coverage through current employment, you will typically use Form CMS-40B to apply for Part B and Form CMS-L564 to document the employer coverage that allowed you to delay enrollment.
Your employer normally completes part of the CMS-L564 form. These forms help Medicare determine that you qualify for a Special Enrollment Period and can enroll without a late-enrollment penalty.
LET’S LOOK AT YOUR SPECIFIC SITUATION
Get Your Personalized Medicare Blueprint
Every situation is different. We’ll review your current coverage, answer your questions, and create a clear plan based on your needs and priorities.
No cost for our help. No pressure. Just clear Medicare guidance.
CENTRAL OHIO MEDICARE HELP
Helping people across Central Ohio understand Medicare and make informed coverage decisions.
MEDICARE
Medicare Basics
Medicare Advantage
Medicare Supplements
Prescription Drug Plans
Working Past 65
Costs & Coverage
RESCOURCES
Medicare Articles
Medicare Videos
FAQs
Important Forms
Plan Finder Tool
COMPANY
About Us
Contact Us
We have no affiliation with and no endorsement from the United States government or the federal Medicare program. We don't sell every plan on the market in your area. What we share is limited to the plans we're appointed to offer here. Contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP) for information about all of your options.
© 2026 Hill Insurance Group. All rights reserved.
Privacy Policy | Terms of Use | Non-Discrimination Notice