Medicare 2026

Still Working at 65 in Omaha? How Medicare Fits With Job Coverage

OMAHA, Neb. — Turning 65 used to mean retirement was right around the corner. Not anymore. Plenty of Omahans are still clocking in at 65, 68, even 70 — and that raises a very real question: do you need to sign up for Medicare if you already have health insurance through work?

The answer is "it depends," and getting it wrong can cost you a lifetime late-enrollment penalty. Here's how to think it through.

First, ask how big your employer is

The size of the company you (or your spouse) work for is the single most important factor.

• 20 or more employees: Your employer's group health plan generally pays first, and Medicare pays second if you enroll. In most cases, you can safely delay Part B without a penalty as long as you stay covered by that plan through active employment.
• Fewer than 20 employees: Medicare usually pays first, and your employer's plan pays second. That means if you don't sign up for Medicare at 65, you could be left with big gaps — because your employer plan may only cover what Medicare would have covered.

If you're not sure which category your employer falls into, ask your HR or benefits office in writing. This is one question worth pinning down early.

Part A is usually a no-brainer

Most people qualify for premium-free Part A (hospital insurance) because they or their spouse paid Medicare taxes for at least 10 years. If that's you, enrolling in Part A at 65 typically doesn't cost anything and can act as secondary coverage for hospital stays.

One important exception: if you contribute to a Health Savings Account (HSA), you cannot keep making HSA contributions once you enroll in any part of Medicare, including Part A. If your HSA is a big part of your retirement strategy, talk with your benefits team before signing up.

Part B is where the timing matters

Part B (doctor visits and outpatient care) comes with a monthly premium, so many workers with solid job coverage choose to delay it. That's often fine — if your employer has 20 or more employees and the coverage counts as "creditable."

When you eventually leave that job or lose that coverage, you get a Special Enrollment Period of up to 8 months to sign up for Part B without a late penalty. Miss that window, and the penalty is 10% added to your premium for every 12 months you could have had Part B but didn't — for life.

COBRA and retiree coverage do not count as active employer coverage for this purpose. That's one of the most common — and most expensive — Medicare mistakes.

Don't forget Part D (drug coverage)

If you delay Medicare because you have employer coverage, check whether your workplace drug coverage is "creditable" — meaning it's at least as good as standard Medicare Part D. Your plan is required to send you a notice about this each year. Keep it.

If your job coverage is creditable, you can wait to enroll in Part D without a penalty. If it isn't, you'll want to sign up for a Part D plan when you first become eligible.

A few 2026 numbers worth knowing:

• The Part D out-of-pocket cap is $2,100 in 2026 — once you hit that in covered drug costs, you pay $0 for the rest of the year.
• The Part D maximum deductible is $615.
• The old "donut hole" coverage gap is gone as of 2025; Part D now has three simpler phases.
• The Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly installments if you'd rather not pay big bills all at once.
• Higher earners pay IRMAA surcharges on Part B and Part D premiums; those begin above $109,000 in income for a single filer in 2026.

What's available around Omaha

Omaha sits in Douglas County, and Medicare Advantage and Part D plan availability is set at the county level. If and when you do transition off employer coverage, you'll have choices — including Original Medicare with a stand-alone Part D plan (and often a Medigap policy), or a Medicare Advantage plan that bundles hospital, medical, and usually drug coverage together.

You can compare what's offered in Douglas County using the Plan Finder at Medicare.gov. Nebraska SHIIP (the state's SHIP counselors) can also walk you through it for free — no sales pressure.

Key enrollment windows to remember

• Initial Enrollment Period: the 7-month window around your 65th birthday.
• Special Enrollment Period: up to 8 months after employer coverage ends, for Part B.
• Annual Enrollment Period: October 15 – December 7 each year, for Part D and Medicare Advantage changes.
• Medicare Advantage Open Enrollment: January 1 – March 31, if you're already in an Advantage plan and want to switch.