Your Situation
Still Working Past 65 — Do You Need Medicare Yet?
If you're still working at 65 and covered by a health plan at work, you may be able to delay part of Medicare without a penalty. But the answer depends on the size of your employer, whether you have an HSA, and what your work coverage costs you.
The Big Question: How Many Employees?
The size of your employer decides who pays first — Medicare or your work plan. That decides whether you can safely delay Part B.
20 or more employees
Your work plan pays first. Medicare would pay second.
You can usually delay Part B with no penalty for as long as you (or your spouse) are still working and covered by that plan.
Fewer than 20 employees
Medicare pays first. Your work plan pays second — and may pay little or nothing if you don't have Medicare.
You generally need to sign up for Parts A and B at 65, even though you're still working. Ask your employer or plan in writing how they coordinate with Medicare.
Coverage through your spouse's current job counts the same way, based on the size of your spouse's employer.
The coverage has to come from current, active employment. COBRA, retiree coverage, and Marketplace (ACA) plans do not let you delay Part B without a penalty.
Self-employed or covered by an individual plan? That is not employer coverage for Medicare purposes — plan to enroll at 65.
Part A: Usually Worth Taking — Unless You Have an HSA
Most people pay no premium for Part A, so many workers sign up for it at 65 and keep their job coverage too. Part A can help pay for a hospital stay alongside your work plan.
If you contribute to a Health Savings Account (HSA)
- Once any part of Medicare starts — including Part A — you can no longer put money into an HSA. You can still spend what's already in it.
- If you sign up for Part A after 65, it usually starts up to 6 months earlier than the month you apply (but not before the month you turned 65). Stop HSA contributions 6 months before you apply to avoid a tax penalty.
- Starting Social Security automatically enrolls you in Part A. If you want to keep funding your HSA, hold off on Social Security too.
Your HSA is a tax question as well as a Medicare one — check with your tax professional before you change contributions.
Drug Coverage: Look for the "Creditable" Notice
To delay Part D without a penalty, your work drug coverage has to be creditable — meaning it's expected to pay at least as much as a standard Medicare drug plan. Your employer must send you a notice saying whether it is, usually each fall before October 15. Keep these notices. If you're asked later to prove you had drug coverage, they're your evidence.
Sometimes Medicare Costs Less Than Your Work Plan
Just because you can stay on your employer plan doesn't mean you should. It's worth comparing.
Compare what you pay
Look at your share of the work premium, your deductible, and your out-of-pocket maximum. Then compare that to Part B ($202.90/month in 2026) plus a Medicare Advantage plan or a Medicare Supplement and drug plan.
Covering a spouse costs more
If your work plan also covers a younger spouse, dropping it may mean your spouse needs their own coverage. Factor in what a Marketplace (ACA) plan would cost them.
Higher income? Check IRMAA
If your income is high, you may pay more than the standard Part B premium. That can tip the math toward staying on your work plan.
Timing your Medigap window
Your 6-month Medicare Supplement open enrollment starts the month your Part B begins — and it only happens once. Don't start Part B early unless you're ready to use your Medicare coverage.
Estimate your monthly Medicare costs → | See the IRMAA income brackets →
When You Do Stop Working
When your job or your work coverage ends — whichever happens first — you get an 8-month Special Enrollment Period to sign up for Part B with no penalty. You'll have 63 days to get drug coverage.
Get your employer to fill out Form CMS-L564
This form proves you had work coverage. Your HR department completes it.
Apply for Part B with Form CMS-40B
Submit both forms to Social Security online, by mail, or at your local office. Apply a month or two before your work coverage ends so there's no gap.
Choose your Medicare coverage
Pick Medicare Advantage or a Medicare Supplement plus a drug plan, so it starts the day your work coverage ends.
Report the income drop if it affects IRMAA
If you were paying more for Part B because of high income, retiring is a life-changing event. Form SSA-44 asks Social Security to use your new, lower income.
Part B – Medical
Enrollment, costs, and late penalties →
My Medicare Timeline
See your enrollment dates →
Still have questions? Talk with Marit.
Licensed Wisconsin agent in downtown Appleton. No cost to talk, no pressure to enroll.
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