Medicare 2026

Working past 65 in Elsmere? How Medicare and your job plan fit together

ELSMERE, Del. — Turning 65 used to mean retiring. Today, plenty of people in Elsmere are still clocking in, still covered by a workplace health plan, and still wondering what to do about Medicare. The good news: you often have choices. The trickier news: the right move depends on the size of your employer, the kind of coverage you have, and a few deadlines you don't want to miss.

Here is a plain-English guide to how Medicare works alongside job-based coverage — and how to think through the decision.

First, the basics of who pays first

When you have both Medicare and job-based insurance, one plan is the "primary payer" and the other is "secondary." Which is which comes down mostly to how many people your employer employs.

• Fewer than 20 employees: Medicare generally pays first. Your group plan pays second. In this case, not signing up for Part B at 65 can leave you with big gaps, because the employer plan expects Medicare to cover its share.
• 20 or more employees: Your group health plan generally pays first, and Medicare pays second. Many people in this situation delay Part B until they retire or leave the plan.

If you're not sure which rule applies to you, your HR or benefits office can tell you in writing. That answer drives almost every other decision on this page.

Part A is usually a yes. Part B is the real choice.

Most people qualify for premium-free Part A (hospital insurance) because they or a spouse paid Medicare taxes long enough. If that's you, signing up for Part A at 65 is common, even while you're still working — it can pick up some hospital costs your job plan doesn't.

There's one big exception: if you contribute to a Health Savings Account (HSA), you must stop those contributions once any part of Medicare begins, including Part A. If your HSA is important to you, talk to your benefits office before enrolling.

Part B (doctor and outpatient care) has a monthly premium. Whether to take it while working depends on:

• Employer size (see above),
• How good your job coverage is,
• Whether your spouse or dependents also rely on your plan,
• Your income (higher earners pay an IRMAA surcharge; in 2026 that starts above $109,000 for a single filer).

The Special Enrollment Period that protects you

If you delay Part B because you have qualifying job-based coverage from current work, you get an 8-month Special Enrollment Period to sign up once that employment or coverage ends — whichever comes first. Sign up during that window and you avoid the Part B late-enrollment penalty.

Two things trip people up: 1. COBRA and retiree coverage do not count as active employer coverage for this rule. The 8-month clock starts when your job ends, not when COBRA ends. 2. You have to actually enroll. The SEP is a right, not automatic.

What about drug coverage (Part D)?

If your job plan includes prescription drugs, ask HR each year for a "creditable coverage" notice. That letter tells you whether your workplace drug coverage is at least as good as Medicare's. As long as it's creditable, you can delay Part D without a late penalty.

A few numbers worth knowing if you do move to Part D later:

• The Part D out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027.
• The maximum Part D deductible is $615 in 2026 and $700 in 2027.
• The old "donut hole" is gone — Part D now has three phases.
• The Medicare Prescription Payment Plan lets you spread drug costs into monthly payments if you choose.

How this plays out in Elsmere

Elsmere is in New Castle County, where a wide range of Medicare Advantage and Part D plans are sold each year. If and when you leave your job plan behind, you'll be choosing from that county-level lineup — either Original Medicare (with or without a Medigap policy and a stand-alone Part D plan) or a Medicare Advantage plan that bundles things together.

You don't have to figure it out alone. Delaware's State Health Insurance Assistance Program (SHIP), called ELDERinfo, offers free, unbiased counseling to Delaware residents.

A simple way to decide

Ask yourself, in order: 1. How big is my employer? Under 20 or 20+? That sets who pays first. 2. Do I have an HSA I want to keep funding? If yes, weigh that against enrolling in Part A. 3. Is my drug coverage creditable? Get the notice in writing every year. 4. Who else is on my plan? Family coverage may tip the decision toward staying on the job plan longer. 5. When my job coverage ends, do I know my 8-month window? Put it on the calendar.

Keep in mind the standard Medicare calendar too: the Annual Enrollment Period runs Oct. 15 – Dec. 7 each year, and the Medicare Advantage Open Enrollment Period runs Jan. 1 – March 31 for people already in an Advantage plan.