Medicare Part D

How Winston Salem Retirees Avoid Medicare Late Penalties

WINSTON-SALEM, N.C. — Turning 65 comes with a lot of paperwork, and Medicare has one rule that surprises people every year: miss the wrong sign-up window, and you could pay a penalty every month for as long as you have coverage.

The good news is that these deadlines are simple once you know them. Here is how the timing works, and how Winston-Salem residents can avoid a mistake that lasts a lifetime.

Why Medicare's deadlines matter so much

Most bills you pay in life are one-time. Medicare's late-enrollment penalties are different. If you sign up for Part B (doctor visits and outpatient care) or Part D (prescription drugs) after you were supposed to, the penalty gets added to your monthly premium — and it usually stays there for the rest of your life.

That's why understanding the enrollment windows before your 65th birthday is one of the most important financial decisions you'll ever make.

Your first window: the Initial Enrollment Period

When you first become eligible for Medicare, you get a seven-month window called your Initial Enrollment Period. It starts three months before the month you turn 65, includes your birthday month, and ends three months after.

If you sign up during those seven months, you avoid late penalties. According to Medicare.gov, this is the cleanest way to start coverage without any long-term cost.

If you're still working at 65 and have solid health coverage through your job (or your spouse's job), you may be able to delay Part B without penalty. That's called a Special Enrollment Period, and it kicks in when your job-based coverage ends.

How the Part B late penalty works

If you don't sign up for Part B when you're first eligible — and you don't qualify for a Special Enrollment Period — here's what happens:

• Your monthly Part B premium goes up 10% for each full 12-month period you could have had Part B but didn't.
• That higher premium sticks with you for as long as you have Part B.

So a two-year delay means paying 20% extra, every month, for life. A four-year delay means 40% extra. The math adds up quickly.

How the Part D late penalty works

Part D covers prescription drugs, and it has its own penalty. If you go 63 days or more in a row without Part D or other "creditable" drug coverage (coverage at least as good as Medicare's), you can be charged a penalty when you eventually enroll.

The penalty is 1% of the "national base beneficiary premium" for every month you went without coverage, added to your monthly Part D premium — again, for as long as you have the plan.

A quick tip: if your employer or union plan includes drug coverage, ask them each year for a "creditable coverage" notice. Keep it. That paperwork is your proof if Medicare ever asks.

What 2027 looks like for drug coverage

Even if penalties aren't your concern, Part D is changing in ways worth knowing about:

• The out-of-pocket cap for Part D is $2,100 in 2026 and $2,400 in 2027. Once you spend that much on covered drugs, you pay nothing more for the rest of the year.
• The maximum Part D deductible is $615 in 2026 and $700 in 2027.
• The old "donut hole" coverage gap was eliminated in 2025, so Part D now has three simpler phases instead of four.
• The Medicare Prescription Payment Plan lets you spread your drug costs across the calendar year in monthly installments, instead of paying big amounts all at once at the pharmacy.

These are program-level rules set by CMS — they apply nationwide, including here in Winston-Salem.

What's available locally

Winston-Salem is in Forsyth County, where Medicare beneficiaries can compare Medicare Advantage plans, standalone Part D plans, and Medigap options offered in the county. Plan availability is set at the county level, not the city level, so the official plan finder at Medicare.gov will show you exactly what's offered where you live once you enter your ZIP code.

Two dates to keep on your calendar:

• Annual Enrollment Period: October 15 – December 7. This is when anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan.
• Medicare Advantage Open Enrollment: January 1 – March 31. If you're already in a Medicare Advantage plan, you get one chance during this window to switch to a different one or return to Original Medicare.

A quick note on higher-income surcharges

If your income is above certain levels, you'll pay an extra amount on top of your Part B and Part D premiums. This is called IRMAA. For 2026, IRMAA surcharges begin above $109,000 in income for a single filer (higher thresholds apply for married couples filing jointly). Social Security uses your tax return from two years earlier to decide.

This isn't a penalty — it's an income-based adjustment — but it's worth knowing about when you plan your retirement budget.