Medicare 2026

Working past 65 in Virginia Beach? How employer size decides who pays first

VIRGINIA BEACH, Va. — Plenty of people in Virginia Beach are still clocking in past their 65th birthday, and a lot of them are asking the same question: do I have to sign up for Medicare now, or can I stay on the plan from work? The short answer is that it depends less on your age and more on how many people your employer has on the payroll.

That single number — the size of the workforce — is what decides which insurance pays your bills first, and whether delaying Medicare could cost you a late penalty down the road.

Start with the size of your employer

Medicare uses a rule called "coordination of benefits" to decide which plan pays first when you have two. For people still working, the deciding factor is how many employees are on staff.

If your employer (or your spouse's employer, if you are covered through them) has 20 or more employees, the group health plan is the primary payer. Medicare, if you are enrolled, pays second.

If the employer has fewer than 20 employees, Medicare is usually primary and the group plan pays second. In that situation, you generally need to be enrolled in Medicare Part A and Part B, because the employer plan expects Medicare to cover its share first. Skipping Part B here can leave you with big gaps.

Ask your benefits office in writing which one applies to you. It matters more than almost any other question you will ask about your coverage.

Part A is usually a yes, even if you keep working

Most people qualify for premium-free Part A (hospital insurance) because they or their spouse paid Medicare taxes for at least 10 years. Because there is no monthly cost, many workers go ahead and enroll in Part A at 65 even while keeping employer insurance.

One important exception: if you contribute to a Health Savings Account (HSA), you cannot keep adding money to it once you enroll in any part of Medicare, including Part A. If your HSA matters to you, talk with your employer before signing up.

Part B is the decision that trips people up

Part B (doctor and outpatient care) has a monthly premium, so it is the one people weigh most carefully. Here is the rule that keeps you safe:

You can delay Part B without a late penalty only if you have "current" group health coverage based on active employment — yours or a spouse's. Retiree coverage, severance health benefits and COBRA do not count as current employer coverage for this purpose, even though they may feel like real insurance.

When the job or the coverage ends, Medicare gives you a Special Enrollment Period of up to 8 months to sign up for Part B without paying more. Miss that window and the Part B late enrollment penalty can stick with you for life — typically 10% added to your premium for each 12-month period you could have had it but did not.

Don't forget Part D — drug coverage counts too

Part D covers prescriptions, and it has its own late penalty if you go without "creditable" drug coverage for 63 days or more after you first become eligible.

Your employer plan should send you a notice of creditable coverage each year telling you whether its drug benefits are at least as good as Medicare's. Save that notice. If your job coverage is creditable, you can keep it and delay Part D. If it isn't, look into a Part D plan to avoid the penalty.

The Part D maximum deductible is $615 in 2026 and $700 in 2027, and the out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027. The old "donut hole" coverage gap was eliminated in 2025. There is also an optional Medicare Prescription Payment Plan that lets you spread your drug costs across the year in monthly installments.

When employer coverage ends: your 8-month window

Virginia Beach is in Virginia Beach city, an independent city under Virginia law, and Medicare plan availability there is set at that county-equivalent level. Whatever the local plan lineup looks like in a given year, the enrollment timing rules are federal and the same everywhere:

• 8 months to enroll in Part B after your job or employer coverage ends (whichever comes first), without a penalty.
• 63 days to pick up creditable drug coverage before Part D penalties start.
• The Annual Enrollment Period runs Oct. 15 – Dec. 7 each year for changes to Medicare Advantage and Part D.
• The Medicare Advantage Open Enrollment Period runs Jan. 1 – March 31 for people already in a Medicare Advantage plan.

One more thing to know if you are a higher earner: in 2026, income-related premium surcharges (IRMAA) on Part B and Part D begin above $109,000 for a single filer, based on your tax return from two years earlier.