Medicare 2026

Medicare and Employer Coverage in Brattleboro After 65

BRATTLEBORO, Vt. — Plenty of workers around Brattleboro are staying on the job well past 65, and that raises a fair question: do you have to sign up for Medicare right now, or can it wait until you actually retire? The answer depends on the size of your employer, the kind of coverage you have, and a few deadlines that are easy to miss.

Start with employer size

The single most important detail is how many people work for your employer. Medicare uses that number to decide who pays first when you have a claim.

If your employer (or your spouse's employer, if you're covered through them) has 20 or more employees, the group health plan generally pays first and Medicare pays second. In that case, many workers choose to delay Part B and keep the job coverage as their main insurance.

If the employer has fewer than 20 employees, Medicare usually pays first. That means you typically need to enroll in Part A and Part B when you're first eligible, or your job-based plan may pay very little — even if you're still using it every day.

If you're not sure which rule applies to you, ask your HR or benefits office in writing. This is the question Medicare's own guides tell you to ask.

Part A is usually the easy call

Most people qualify for premium-free Part A (hospital insurance) based on their own or a spouse's work history. If that's you, signing up at 65 is often harmless — it can help fill in around your employer plan.

There's one big exception: if you contribute to a Health Savings Account (HSA), you (and your employer) must stop contributions once any part of Medicare starts. Part A enrollment is also backdated up to six months, so plan the timing carefully with your benefits team.

Part B is where the deadlines bite

Part B (doctor and outpatient care) is where people most often get tripped up. If you don't have qualifying employer coverage and you delay Part B, you can face a late enrollment penalty that sticks with you for life — an extra 10% added to your monthly premium for each full 12-month period you could have had it but didn't.

The good news: if you've been covered by a qualifying employer group health plan through active employment, you get a Special Enrollment Period to sign up for Part B:

• Up to 8 months after the employment or the group coverage ends, whichever comes first.
• COBRA and retiree coverage do not count as active employer coverage for this purpose. The clock starts when the job ends, not when COBRA ends.

Part D and prescription drugs

Part D is prescription drug coverage. If your employer plan includes drug coverage that Medicare considers creditable (at least as good as standard Part D), you can delay Part D without penalty. Your plan is required to send you a notice each year telling you whether it's creditable — keep those letters.

A few Part D facts worth knowing as you plan:

• The annual out-of-pocket cap for Part D drugs is $2,100 in 2026.
• The maximum Part D deductible is $615.
• The old coverage gap ("donut hole") is gone as of 2025; there are now three payment phases.
• The Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly installments if you choose.

Higher earners: watch for IRMAA

If your income is above certain thresholds, you'll pay an Income-Related Monthly Adjustment Amount (IRMAA) on top of your Part B and Part D premiums. For 2026, IRMAA begins above $109,000 for a single filer (higher for joint filers). Medicare looks back two years at your tax return, so a big work year now can affect your Medicare premiums later.

What Brattleboro workers should know locally

Brattleboro is in Windham County, where Medicare Advantage and Part D plan availability is set at the county level. If and when you decide to leave your employer plan and shop Medicare coverage, the plans you can choose from are the ones offered in Windham County — not statewide. You can compare them at medicare.gov using your ZIP code.

Two dates to keep on the calendar:

• Annual Enrollment Period: October 15 – December 7 (make Medicare Advantage and Part D changes for the following year).
• Medicare Advantage Open Enrollment: January 1 – March 31 (one switch allowed if you're already in a Medicare Advantage plan).

A simple planning checklist

• Ask HR whether your employer has 20+ employees and whether your drug coverage is creditable.
• Decide whether to enroll in Part A at 65 — and stop HSA contributions if you do.
• Mark the 8-month Part B Special Enrollment window on the day your job coverage ends.
• Save all creditable-coverage notices in case you need to prove them later.