Medicare 2026

Working past 65 in Greenville? How to time Medicare around your job

GREENVILLE, S.C. — More people are working into their late 60s and early 70s, and that raises a question the Medicare handbook does not always answer clearly: if you already have health insurance through your job, do you have to sign up for Medicare at 65?

The short answer is: it depends on the size of your employer, the kind of coverage you have, and whether that coverage counts as "creditable" under Medicare rules. Getting the timing right can spare you late penalties that stick with you for life.

Start with the size of your employer

The single biggest factor is how many people work at the company providing your health plan.

If your employer has fewer than 20 employees, Medicare is generally the primary payer once you turn 65. That means your group plan expects Medicare to pay first, and it fills in second. If you skip Part B in that situation, you could be left paying most of your medical bills yourself.

If your employer has 20 or more employees, your group health plan is usually primary, and Medicare is secondary. In that case, many people choose to delay Part B until they retire or lose the group coverage.

Rules can be different for retiree coverage, COBRA and TRICARE, so check with your benefits administrator before you decide.

Part A is usually free — but not always

Most people qualify for premium-free Part A (hospital insurance) at 65 because they or a spouse paid Medicare taxes long enough. If that's you, signing up for Part A when you turn 65 is often a reasonable step, even if you keep your job coverage.

There is one important exception. If you contribute to a Health Savings Account (HSA), enrolling in any part of Medicare — including Part A — stops you from making new HSA contributions. Many workers who plan to keep funding an HSA choose to delay Part A until they leave the employer plan. You can still spend money already in the HSA on qualified expenses.

Part B and the late enrollment penalty

Part B (doctor and outpatient care) has a monthly premium and, for most people, a late enrollment penalty if you sign up after you were first eligible without having other creditable coverage.

The penalty is 10% added to your Part B premium for each full 12-month period you could have had Part B but didn't — and it typically lasts as long as you have Medicare.

Here's the relief valve: if you had group health coverage through current employment (yours or your spouse's) at a company with 20 or more employees, you generally qualify for a Special Enrollment Period. You have up to 8 months after the employment or the group coverage ends — whichever is first — to sign up for Part B without a penalty. COBRA and retiree coverage do not extend this window.

Don't forget Part D

Part D covers prescription drugs, and it has its own late enrollment penalty. To avoid it, you need "creditable" drug coverage — coverage that Medicare considers at least as good as a standard Part D plan.

Employer plans often are creditable, but not always. Your plan administrator is required to send you a notice each year that says whether the drug coverage is creditable. Keep those notices. If you drop your job coverage later, you'll want to sign up for a Part D plan within 63 days to avoid the penalty.

For 2026, Part D has a $2,100 annual out-of-pocket cap on covered drugs and a maximum deductible of $615. The old "donut hole" coverage gap has been eliminated as of 2025, replaced by a simpler three-phase design. Medicare also offers an optional Prescription Payment Plan that lets you spread your drug costs across the calendar year in monthly payments.

What Greenville workers should know locally

Greenville is in Greenville County, where Medicare beneficiaries have a range of Original Medicare, Medicare Advantage, Part D and Medigap options available through CMS. Plan choices are set at the county level, not the city level, so two neighbors on opposite sides of a county line may see different lineups.

If you're still working, availability matters less on day one — your employer plan is doing the heavy lifting — but it's worth knowing what's out there before your retirement date. The Annual Enrollment Period runs October 15 through December 7, and the Medicare Advantage Open Enrollment Period runs January 1 through March 31 for people already in an Advantage plan.

One more thing higher earners should watch: IRMAA, the income-related surcharge on Part B and Part D premiums, kicks in above $109,000 in income for a single filer in 2026 (higher for joint filers). It's based on your tax return from two years earlier, so a big work year now can affect Medicare premiums later.