Medicare 2026

Medicare Initial Enrollment Period for Brookline residents

# Turning 65 in Brookline? Don't Miss Your 7-Month…

BROOKLINE, Mass. — If your 65th birthday is on the horizon, you're about to meet a Medicare deadline that shapes the rest of your coverage: your Initial Enrollment Period, or IEP. It's a seven-month window built around your birthday month, and using it well can save you paperwork, penalties, and stress down the road.

Here in Brookline — part of Norfolk County — you have plenty of Medicare choices to sort through when the time comes. But before you compare anything, it helps to understand the basic timeline and the first steps every new enrollee should take.

What the Initial Enrollment Period actually is

Your IEP is a one-time, seven-month window tied to your 65th birthday. It includes:

• The three months before your birthday month
• Your birthday month
• The three months after your birthday month

For most people, this is when you first sign up for Medicare Part A (hospital) and Part B (medical). If you want a Medicare Advantage plan (Part C) or a stand-alone Part D drug plan, you can enroll in one during your IEP too — but only after you have Part A and Part B in place.

When your coverage actually starts

The month you enroll changes your start date. If you sign up in the three months before your birthday month, your Part A and Part B typically begin the first day of your birthday month (or the month before, if your birthday falls on the first). If you wait until your birthday month or later, coverage starts the first day of the month after you enroll.

Translation: enrolling early is the cleanest way to avoid a gap between your old coverage and Medicare.

Do you have to sign up at 65?

Not always. If you're already receiving Social Security benefits, you'll usually be enrolled in Part A and Part B automatically. If you're still working and have creditable employer coverage — through your job or a spouse's job — you may be able to delay Part B without a penalty and enroll later during a Special Enrollment Period.

But "employer coverage" isn't the same as retiree coverage or COBRA. Those generally do not protect you from late-enrollment penalties. If you're not sure where your coverage falls, ask your benefits administrator in writing before your birthday month arrives.

Why missing the window is costly

Skip your IEP without other qualifying coverage, and two things can happen:

• Part B late penalty: 10% added to your monthly Part B premium for every full 12 months you could have had it but didn't — and that surcharge usually lasts as long as you have Part B.
• Part D late penalty: A smaller monthly amount based on how long you went without creditable drug coverage, also generally permanent.

You could also be stuck waiting for the next General Enrollment Period to sign up, which delays your coverage further.

First steps to take right now

You don't have to figure everything out at once. A simple order of operations helps:

1. Mark your seven-month window on the calendar. 2. Check your current coverage. If you have employer insurance, ask HR whether it's considered "creditable" for Medicare purposes. 3. Decide how you want Medicare delivered — Original Medicare (Parts A and B, often paired with a stand-alone Part D plan and possibly a Medigap policy) or a Medicare Advantage plan that bundles coverage. 4. Look at your prescriptions. The Part D annual out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027. The Part D maximum deductible is $615 in 2026 and $700 in 2027. The old "donut hole" coverage gap was eliminated in 2025, so drug coverage now has three phases instead of four. An optional Medicare Prescription Payment Plan lets you spread drug costs across the year in monthly installments. 5. Compare what's available locally. Brookline is in Norfolk County, where a wide range of Medicare Advantage and Part D plans are offered each year. Plan menus can change every fall — the 2027 lineup is detailed in each plan's Annual Notice of Change and on Medicare's Plan Finder at Medicare.gov.

A quick note on income and IRMAA

If your income is higher than average, be aware of the Income-Related Monthly Adjustment Amount, or IRMAA. In 2026, IRMAA surcharges on Part B and Part D begin for single filers with income above $109,000 (higher for joint filers). Social Security uses your tax return from two years earlier to decide, so a big one-time income event can affect your Medicare premiums later.

Where Brookline residents can get help

You don't have to navigate this alone, and you don't need to pay anyone for basic guidance.

• Medicare.gov — official plan comparisons and enrollment.
• 1-800-MEDICARE (1-800-633-4227) — 24/7 help line.
• SHINE (Serving Health Insurance Needs of Everyone) — Massachusetts' free SHIP counseling program, with trained volunteers who can meet with you one-on-one.
• Social Security Administration — for actually signing up for Part A and Part B, at SSA.gov or 1-800-772-1213.