Medicare 2026

Still Working at 65? How Medicare Fits With Job Coverage

OZARK, Mo. — Turning 65 used to mean retiring. Not anymore. Plenty of folks in Ozark are still clocking in — running businesses along the Highway 65 corridor, teaching, nursing, or working part-time at the shops near Finley River Park. If that sounds like you, one of the biggest questions on your mind is probably this: Do I have to sign up for Medicare at 65 if my employer still covers me?

The short answer is: it depends on the size of your employer. And getting it wrong can lead to lifelong penalties or a gap in coverage. Here is what to know.

The rule that decides everything: employer size

Medicare uses a simple test to figure out who pays first — your job's health plan or Medicare.

• If your employer has 20 or more employees, your group health plan generally pays first, and Medicare pays second. You can usually delay signing up for Part B without penalty while you keep that job-based coverage.
• If your employer has fewer than 20 employees, Medicare typically pays first. In that case, you usually need to enroll in Part A and Part B when you first become eligible, or your employer coverage may pay very little of your bills.

That second scenario catches a lot of small-business workers off guard. If you work for a shop with a handful of employees in Christian County, ask your HR contact or benefits administrator — in writing — whether Medicare is expected to be primary.

Part A is almost always a yes

Most people qualify for premium-free Part A (hospital insurance) because they or a spouse paid Medicare taxes for at least 10 years. Since it doesn't cost anything, many workers enroll in Part A at 65 even if they keep their job coverage.

One important exception: if you contribute to a Health Savings Account (HSA), you cannot keep contributing once you enroll in any part of Medicare, including Part A. If your HSA matters to you, talk with your benefits office before enrolling.

Part B — the piece with the biggest penalty risk

Part B (doctor visits, outpatient care) has a monthly premium, so many working people delay it. That's fine if your employer coverage counts as "creditable" and the employer has 20+ employees.

When you eventually leave that job or lose the coverage, you get an 8-month Special Enrollment Period to sign up for Part B without a late penalty. Miss that window, and you could pay a 10% premium penalty for every 12 months you were eligible but didn't enroll — for life.

If you're a higher earner, keep in mind that IRMAA surcharges kick in above $109,000 in income for a single filer in 2026, which raises your Part B and Part D premiums.

Part D and prescription drugs

If your job's plan includes drug coverage that Medicare considers "creditable," you can delay Part D too. Your employer or plan should send you a Notice of Creditable Coverage every year — save it.

If your workplace drug coverage isn't creditable and you go without Part D for more than 63 days, you'll face a permanent Part D late penalty.

A few 2026 Part D facts worth knowing whether you enroll now or later:

• The out-of-pocket cap is $2,100 for the year.
• The maximum deductible is $615.
• The old "donut hole" is gone — Part D now has three simpler phases.
• The Medicare Prescription Payment Plan lets you spread your drug costs into monthly payments instead of paying all at once at the pharmacy.

What's available around Ozark

Ozark is in Christian County, where Medicare-eligible residents have access to Original Medicare plus a range of Medicare Advantage and stand-alone Part D options offered by private insurers. Availability and specifics are set at the county level, so two neighbors on the same street see the same menu of choices.

If you're still working and happy with your employer plan, you don't have to make a Medicare Advantage or Part D decision today. But it's worth understanding your options for when you do retire — especially around the Annual Enrollment Period, October 15 through December 7, and the Medicare Advantage Open Enrollment Period, January 1 through March 31.