Medicare 2026

Still Working at 65 in Wilmington? How Medicare Fits In

WILMINGTON, Del. — Turning 65 used to mean a gold watch and a retirement party. Today, plenty of Delawareans are still clocking in — running businesses downtown, teaching, working at the hospitals, or logging hours at one of the big employers along the I-95 corridor. If that's you, Medicare gets more confusing, not less. Do you have to sign up? Can you keep your job's health plan? What happens if you get it wrong?

Still working at 65? Here's how Medicare and your job's coverage fit together

The good news: the rules are clearer than they look once you know two things — the size of your employer, and how Medicare "coordinates" with the coverage you already have.

Start with one question: how big is your employer?

Medicare's rules hinge on your employer's size, because that decides which insurance pays first (the "primary payer") and which pays second.

• 20 or more employees: Your employer's group health plan is primary. Medicare would be secondary if you enrolled. Many people in this situation delay Part B to avoid paying a premium for coverage they don't yet need.
• Fewer than 20 employees: Medicare is generally primary once you're eligible, and your employer plan pays second. In this case, most people should enroll in Part A and Part B at 65, or risk large gaps in coverage.

If you're not sure which category you fall into, your HR or benefits office can tell you in one sentence. Ask them directly: "Is our plan primary or secondary to Medicare for employees 65 and older?"

Part A is usually an easy yes

Most people qualify for premium-free Part A (hospital insurance) because they or a spouse paid Medicare taxes for at least 10 years. If that's you, signing up for Part A at 65 is usually harmless — it can act as secondary coverage for hospital stays and costs you nothing in premiums.

There's 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 team before you enroll.

Part B is the real decision

Part B (doctor visits and outpatient care) has a monthly premium, so this is where the real coordination question lives.

• If your employer plan is primary (20+ employees) and you like the coverage, you can generally delay Part B without penalty, as long as your employer coverage is considered "active" — not retiree coverage and not COBRA.
• When you eventually leave the job or lose that coverage, you get an 8-month Special Enrollment Period to sign up for Part B without a late penalty. Don't wait — COBRA and retiree plans do not count as active employer coverage for this purpose, and that's where people get tripped up.
• If your employer plan is secondary (under 20 employees), skipping Part B can leave you with big out-of-pocket bills, because your job's plan expects Medicare to be paying the lion's share.

The late-enrollment penalty for Part B is permanent — it's added to your premium for as long as you have Medicare — so this decision is worth getting right the first time.

Don't forget Part D (drug coverage)

If your employer plan includes prescription drugs, check whether that coverage is "creditable" — meaning at least as good as standard Medicare Part D. Your plan is required to send you a notice each year telling you. Keep that letter.

• If your drug coverage is creditable, you can delay Part D with no penalty.
• If it's not, and you go more than 63 days without creditable coverage, you'll owe a Part D late penalty for life once you finally enroll.

A few Part D facts worth knowing for 2026: the annual out-of-pocket cap on covered drugs is $2,100, the maximum deductible is $615, and the old "donut hole" is gone — replaced by a simpler three-phase structure. There's also an optional Medicare Prescription Payment Plan that lets you spread drug costs across monthly payments instead of paying a big bill at the pharmacy counter.

What Wilmington workers should know locally

Wilmington sits in New Castle County, where Medicare beneficiaries have access to Original Medicare (Parts A and B) plus a range of Medicare Advantage and stand-alone Part D plans offered by multiple carriers. Plan availability is set at the county level by the Centers for Medicare & Medicaid Services (CMS), so the choices you'll see are the same whether you live near Trolley Square, off Concord Pike, or down in the city.

Two dates to keep on your calendar:

• Oct. 15 – Dec. 7: Medicare's Annual Enrollment Period, when you can join, switch, or drop Medicare Advantage and Part D plans.
• Jan. 1 – March 31: Medicare Advantage Open Enrollment, for people already in an Advantage plan who want to change.

One more note for higher earners: if your income is above $109,000 as a single filer (or $218,000 for a couple) in 2026, you may pay an income-related surcharge (IRMAA) on top of your Part B and Part D premiums. That can influence whether it makes sense to delay Part B while you're still working.