Medicare Supplement

Still Working at 65 in Silver Spring? Medicare Rules for 2026

SILVER SPRING, Md. — Turning 65 while still on the job is more common than ever, and it raises a fair question: do you need to sign up for Medicare right away, or can you stay on your employer's health plan? The answer depends on a few things — mainly the size of your employer and how your current coverage works with Medicare.

Here's a plain-English guide to help you think it through.

Start with the size of your employer

Medicare uses employer size to decide who pays first when you have both kinds of coverage.

• 20 or more employees: Your group health plan generally pays first, and Medicare pays second. You can usually delay Part B without penalty while you're still actively working and covered.
• Fewer than 20 employees: Medicare usually pays first. In that case, you'll likely want to enroll in Part A and Part B when you're first eligible, or you could be left with big gaps.

If you're not sure which category your employer falls into, ask your benefits office in writing. This one detail changes almost every decision that follows.

Part A is usually an easy "yes"

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, enrolling in Part A while still working is often a simple move — it can help cover hospital costs your employer plan doesn't.

One important exception: if you contribute to a Health Savings Account (HSA), you must stop HSA contributions once you enroll in any part of Medicare, including Part A. If your HSA matters to you, talk with your benefits team before signing up.

Part B: enroll now, or delay?

Part B covers doctor visits and outpatient care, and it has a monthly premium. Whether to take it at 65 depends on your employer coverage.

• If your employer has 20+ employees and your coverage is considered "creditable," you can usually delay Part B and pick it up later through a Special Enrollment Period — up to 8 months after your job or group coverage ends.
• If your employer is small, delaying Part B can leave you underinsured and could trigger a lifelong late-enrollment penalty.

When in doubt, request the Notice of Creditable Coverage from your employer. Keep that letter — you may need it later to prove you delayed for a valid reason.

Part D and prescription drugs in 2026

Part D covers prescriptions, and there are real changes worth knowing for 2026:

• The out-of-pocket cap for covered drugs is $2,100.
• The maximum Part D deductible is $615.
• The old "donut hole" coverage gap is gone — Part D now has three phases.
• The Medicare Prescription Payment Plan lets you spread your drug costs across the year in monthly amounts instead of paying a big bill at the pharmacy counter.

If your employer plan already includes creditable drug coverage, you can typically delay Part D without penalty. If it doesn't, signing up on time matters — the late penalty sticks with you.

What's available around Silver Spring

Silver Spring is in Montgomery County, where Medicare beneficiaries have a range of options if and when they decide to move off employer coverage — including Original Medicare (Parts A and B), stand-alone Part D drug plans, Medigap (Medicare Supplement) policies, and Medicare Advantage plans. Availability is set at the county level, so your choices are the same across Silver Spring, Bethesda, Rockville and other Montgomery County communities.

You can compare what's offered in your ZIP code using the Plan Finder at medicare.gov.

A quick word on IRMAA

Higher-income enrollees pay an Income-Related Monthly Adjustment Amount (IRMAA) on top of standard Part B and Part D premiums. For 2026, IRMAA starts above $109,000 in income for a single filer (higher thresholds apply for joint filers). If you're still working and earning well, this is worth planning for — Medicare uses your tax return from two years back.

Key dates to remember

• Initial Enrollment Period: the 7-month window around your 65th birthday.
• Special Enrollment Period: up to 8 months after employer coverage ends, if you delayed Part B while working.
• Annual Enrollment Period: October 15 – December 7 each year.
• Medicare Advantage Open Enrollment: January 1 – March 31.