Medicare Supplement

How Medicare Enrollment Order Affects Worcester Workers

If you're still working when you hit 65, you don't automatically have to sign up for everything Medicare offers. But you do have to make some careful choices. The order you enroll — and how your employer coverage fits in — can affect your costs and your access to care for years to come.

Worcester, Mass. — Turning 65 doesn't have to mean leaving your job — or your health plan

Here in Worcester, plenty of people are working well into their late 60s and beyond. If that's you, here's a plain-English guide to how Medicare coordinates with an employer plan, and the common mistakes to sidestep.

Start with Part A — it's usually the easy call

Most people qualify for premium-free Part A (hospital insurance) once they turn 65, because they or a spouse paid Medicare taxes long enough while working. If Part A costs you nothing, many people sign up at 65 even if they keep their job coverage. It acts as secondary insurance for hospital stays.

There's one important exception: if you contribute to a Health Savings Account (HSA), you can no longer add money to it once you enroll in any part of Medicare, including Part A. If your HSA matters to you, talk with your benefits office before signing up.

Part B is where the real decision lives

Part B (doctor visits, outpatient care) has a monthly premium. Whether you should enroll at 65 or delay depends mostly on the size of your employer:

• 20 or more employees: Your employer plan is usually primary, and Medicare is secondary. Many people in this situation delay Part B without a late penalty, because they have "creditable" coverage through work.
• Fewer than 20 employees: Medicare is typically primary, even if you're still on the employer plan. If you don't enroll in Part B on time, your employer coverage may pay very little — leaving you with big bills. In most small-employer situations, you should enroll in Part B at 65.

If you're unsure which category you fall into, ask your HR or benefits contact in writing. This is the single most common mix-up we see.

The Special Enrollment Period protects you — if you use it

If you delay Part B because you had job-based coverage, you get an 8-month Special Enrollment Period (SEP) to sign up after that coverage ends or you stop working — whichever comes first. Miss that window, and you could face a lifetime late-enrollment penalty plus a gap in coverage.

A few things to know:

• COBRA does not count as active employer coverage for this purpose. The 8-month clock starts when your job ends, not when COBRA ends.
• Retiree coverage also doesn't count as active coverage.
• Get any decision to delay in writing from your employer, and keep the paperwork.

Don't forget about prescription drugs

Part D covers prescriptions. If your employer plan includes drug coverage that Medicare considers "creditable" (at least as good as a standard Part D plan), you can delay Part D without penalty. Your employer is required to send you a Creditable Coverage Notice each year — save it.

Some 2026 numbers worth knowing:

• Part D out-of-pocket cap: $2,100 for the year.
• Part D maximum deductible: $615.
• The old coverage gap ("donut hole") is gone as of 2025 — Part D now has three phases.
• The Medicare Prescription Payment Plan lets you spread drug costs into monthly payments across the year, if that helps your budget.

A note on higher incomes (IRMAA)

If your income is on the higher side, expect an Income-Related Monthly Adjustment Amount (IRMAA) added to your Part B and Part D premiums. For 2026, IRMAA begins above $109,000 for a single filer (based on tax returns from two years earlier). Working longer sometimes bumps people into IRMAA territory, so it's worth a look with a tax advisor.

What's actually available in the Worcester area

Worcester is in Worcester County, where Medicare Advantage and Part D plan options are set at the county level by the Centers for Medicare & Medicaid Services (CMS). The specific number of plans and carriers changes each year, so the most current list for your ZIP code lives on the Plan Finder at Medicare.gov. You can also compare Medigap options for Massachusetts there — Massachusetts is one of a few states with its own Medigap rules, which is worth understanding before you switch.

Two key dates to remember:

• Annual Enrollment Period: October 15 – December 7
• Medicare Advantage Open Enrollment: January 1 – March 31