Medicare 2026
Port Chester guide to avoiding Medicare Part B and D penalties
# Medicare late-enrollment penalties: how they work and how to avoid…
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Key takeaways
- Sign up for Part B during your 7-month Initial Enrollment Period, or keep other qualifying coverage, to avoid a lifelong 10% monthly penalty for each 12 months you delay.
- Enroll in a Part D drug plan when first eligible, or maintain "creditable" drug coverage, to avoid a Part D penalty tied to the national base beneficiary premium.
- The Annual Enrollment Period runs October 15 through December 7 each year for Medicare drug and Advantage plan changes.
- For personalized help in Port Chester, contact New York's SHIP program (HIICAP) or call 1-800-MEDICARE.
PORT CHESTER, N.Y. — If you're approaching Medicare age, one of the most important things to understand isn't which plan to pick — it's when to sign up. Miss the right window for Part B or Part D, and you could pay a penalty every month for as long as you have Medicare. The good news: these penalties are avoidable once you know the rules.
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 have other qualifying coverage, like a job-based health plan — you may owe a late-enrollment penalty. For most people, the Part B premium goes up 10% for each full 12-month period you could have had Part B but didn't. And here's the part that stings: you generally pay that higher premium for as long as you have Part B.
Your Initial Enrollment Period is a 7-month window: the three months before you turn 65, your birthday month, and the three months after. If you miss it and don't qualify for a Special Enrollment Period, you may have to wait for the General Enrollment Period (January 1 – March 31) to sign up.
How the Part D late penalty works
The Part D penalty is smaller but works the same way — it stays with you. If you go 63 days or more in a row without Part D or other "creditable" prescription drug coverage after your Initial Enrollment Period, Medicare adds a penalty when you finally enroll.
The amount is 1% of the "national base beneficiary premium" for each full month you went without coverage, rounded to the nearest 10 cents, and it's added to your monthly drug plan premium. Because that base premium can change each year, so does your penalty amount.
What counts as "creditable" coverage
You can delay Part B or Part D without a penalty if you have coverage that Medicare considers just as good. Common examples:
- For Part B: Active employer coverage through your job or your spouse's job, if the employer has 20 or more employees.
- For Part D: Employer or union drug coverage, TRICARE, or VA benefits that meet Medicare's "creditable" standard.
Every fall, your current plan should send you a notice telling you whether your drug coverage is creditable. Keep those letters. If you lose that coverage later, you generally have a Special Enrollment Period to join Medicare without a penalty — but only if you act within the allowed window.
Port Chester: where to get local help
Port Chester is in Westchester County, where retirees have a range of Original Medicare and Medicare Advantage options to consider during enrollment. But before comparing plans, make sure your enrollment timing is right — a penalty follows you no matter which plan you choose.
New York's State Health Insurance Assistance Program is called HIICAP (Health Insurance Information, Counseling and Assistance Program). Counselors are free, unbiased, and not selling anything. Westchester County's Department of Senior Programs and Services runs local HIICAP appointments that Port Chester residents can use.
How to decide: a simple checklist
Ask yourself these questions before your 65th birthday — or before you retire, if you're working past 65:
1. Do I have coverage now, and is it creditable? Check your plan's annual notice, or ask HR. 2. When does my Initial Enrollment Period start and end? Mark the 7-month window on your calendar. 3. If I'm keeping job coverage, do I have written proof? You'll need it later to avoid a penalty. 4. Do I take prescriptions? Even if you don't right now, enrolling in a Part D plan on time protects you from future penalties.
Key dates to remember
- Initial Enrollment Period: The 7 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, for changing Part D or Medicare Advantage plans.
- Medicare Advantage Open Enrollment: January 1 – March 31, for those already in an Advantage plan.
By the numbers
Medicare Part B premium, 2006–2026
The standard monthly Part B premium has climbed from $88.50 in 2006 to $202.90 in 2026. Hover any point for that year’s premium.
Source: CMS. Standard premium shown; in some hold-harmless years many existing enrollees paid less. Confirm at Medicare.gov.
By the numbers
How people get Medicare in Westchester County
(MA penetration in Westchester County)
MA penetration from CMS enrollment data; Medigap share is an estimate. U.S. average is about 54% Medicare Advantage. These are area-level figures, not plan-specific.
Explore
When can you enroll? An interactive year
Enrollment windows are federal and the same nationwide. Confirm your personal dates at Medicare.gov or 1-800-MEDICARE.
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The parts of Medicare
Good to know
Frequently asked questions
How long does the Part B late-enrollment penalty last?
What is the Part D late-enrollment penalty for 2027?
I have coverage through my job past 65. Do I still need to sign up for Medicare?
Where can Port Chester residents get free help understanding penalties?
- CMS — Medicare enrollment periods (medicare.gov)
For personalized answers, contact Medicare.gov, 1-800-MEDICARE, or your local SHIP.
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This page was last updated: September 29, 2026.