Medicare 2026

The Medicare Deadlines That Can Cost You for Life

OSHKOSH, Wis. — Miss the wrong Medicare sign-up window, and the mistake can follow you for the rest of your life. That's the hard truth behind two of the program's most misunderstood rules: the late-enrollment penalties for Part B (doctor visits and outpatient care) and Part D (prescription drugs).

The good news? These penalties are almost always avoidable if you know when to act. Here's a plain-English guide to the deadlines that matter — and how folks in Oshkosh can stay on the right side of them.

What the Part B penalty actually is

If you don't sign up for Part B when you're first eligible — and you don't have other qualifying coverage — Medicare can add 10% to your Part B premium for every full 12-month period you went without it.

That penalty isn't a one-time fee. It's added to your monthly Part B premium for as long as you have Medicare. Someone who waits three years to enroll could pay an extra 30% every month, essentially forever.

Most people become eligible during their Initial Enrollment Period — the seven-month window that starts three months before the month you turn 65 and ends three months after. If you miss it and don't qualify for a Special Enrollment Period, you'll typically have to wait for the General Enrollment Period (January 1 – March 31) to sign up.

What the Part D penalty looks like

Part D has its own penalty, and it works differently. If you go 63 or more days in a row without Part D or other creditable prescription drug coverage after you're first eligible, Medicare can tack a permanent surcharge onto your Part D premium once you do enroll.

The penalty is calculated as 1% of the "national base beneficiary premium" for each month you went without coverage, rounded to the nearest 10 cents, and added to your monthly premium as long as you have Part D.

"Creditable" is the key word. Coverage counts as creditable if it's expected to pay, on average, at least as much as standard Medicare drug coverage. Your employer, union, or retiree plan should send you a notice each year telling you whether your drug coverage qualifies. Save those letters — you may need them later.

The exceptions that can save you

Not everyone has to enroll at 65. If you're still working and covered by an employer group health plan (yours or your spouse's) with 20 or more employees, you can generally delay Part B without penalty and get a Special Enrollment Period when that coverage ends.

The same idea applies to Part D: if your current drug coverage is creditable, you're protected from the late penalty even if you delay signing up.

A few situations where people commonly trip up:

• Retiring but assuming COBRA counts as active coverage for Part B (it usually doesn't).
• Having VA drug benefits and not realizing they count as creditable for Part D (they do).
• Turning 65 while on a Marketplace plan and thinking that delays the clock (it doesn't).

Oshkosh, Winnebago County, and where to get local help

Oshkosh is in Winnebago County, where Medicare beneficiaries have a range of stand-alone Part D plans and Medicare Advantage plans (which include drug coverage) to choose from during enrollment periods. Availability and specifics change each year, and they're set at the county level — not city by city.

For personalized help sorting through the options without a sales pitch, Wisconsin's State Health Insurance Assistance Program (SHIP) — called the Medigap Helpline and the Wisconsin SHIP — offers free, unbiased counseling to Medicare beneficiaries. Local Aging & Disability Resource Centers (ADRCs) can also connect Winnebago County residents with a trained counselor.

Dates to circle in 2026

A few program-wide dates every Medicare beneficiary should know:

• Initial Enrollment Period: The seven months around your 65th birthday.
• General Enrollment Period: January 1 – March 31, for people who missed their initial window.
• Annual Enrollment Period: October 15 – December 7, when you can join, switch, or drop a Medicare Advantage or Part D plan.
• Medicare Advantage Open Enrollment: January 1 – March 31, for people already in an Advantage plan who want to switch once.

Also worth knowing for 2026: Part D's out-of-pocket cap is $2,100, the maximum Part D deductible is $615, and the old "donut hole" is gone — replaced by three simpler coverage phases. Higher-income beneficiaries (above $109,000 for a single filer, based on 2024 tax returns) may also owe IRMAA surcharges on Part B and Part D.