Medicare has
deadlines that
never expire.
Miss a Part B or Part D window and the penalty follows you for life. Pick the wrong Medigap plan in your one open-enrollment period and you may not get another chance to switch without medical underwriting. We work Medicare all year, not just in the fall — and there is never a fee to you for our help.
Four parts, and only two of them come automatically.
Almost every Medicare mistake we see traces back to the same thing: people assume enrolling in Medicare means they are covered. Parts A and B are the government programme. Everything that limits your out-of-pocket exposure — a Supplement, an Advantage plan, a drug plan — you have to go and buy.
Here is the whole structure in four paragraphs. If any of it is already familiar, skip to the Supplement versus Advantage comparison.
Part A — hospital
Inpatient hospital stays, skilled nursing, hospice, some home health. Free if you or a spouse worked about ten years, which covers roughly 99% of people. It is not free of cost sharing, though: in 2026 you pay a $1,736 deductible per benefit period — and a benefit period restarts, so two separate hospitalisations in one year can mean paying it twice.
Part B — doctors and outpatient
Physician visits, outpatient care, labs, durable medical equipment. This one has a monthly premium, usually deducted from your Social Security check. After the annual deductible Medicare pays 80% and you pay 20% — with no annual maximum. That uncapped 20% is why a Supplement or Advantage plan exists at all.
Part C — Medicare Advantage
A private plan that replaces Original Medicare as the payer. It bundles A, B and usually D, adds an out-of-pocket maximum, and often includes dental, vision, hearing and a fitness benefit. In exchange you use the plan's network and its prior-authorisation rules. Compare Advantage and Supplement options.
Part D — prescription drugs
A standalone drug plan, or the drug coverage built into an Advantage plan. Every plan has its own formulary, so the right choice depends entirely on the specific medications you take. Since 2025 there is a hard annual cap on what you can pay out of pocket — $2,100 in 2026. More on Part D drug plans.
Three kinds of Medicare work. One phone number.
Individual coverage, drug plans, and the employer side that most agencies do not touch. We are licensed across the Northeast and hold appointments with the carriers that actually compete here.
Medicare Supplement & Advantage
The core decision, and the one with the longest tail. We price both routes against your doctors, your prescriptions and your travel habits before recommending either.
- Medigap Plan G, Plan N and high-deductible G
- Medicare Advantage HMO, PPO and SNP plans
- Doctor and hospital network verification
- Medigap open enrollment & underwriting rules
- Annual review, not a set-and-forget enrollment
Part D Drug Plans & Penalties
The part people get wrong most often, because the cheapest premium is frequently the most expensive plan once your actual drug list is priced through it.
- Formulary check against your prescriptions
- Total annual cost, not headline premium
- Late-enrollment penalty calculation & appeals
- IRMAA income adjustments and SSA-44 appeals
- Creditable coverage letters from an employer plan
Employer & Retiree Group Medicare
The side of Medicare that lands on an HR desk. We already run the group health plan for employers across the Northeast, so this is the same conversation, not a new vendor.
- Group Medicare Supplement & group MA plans
- Retiree medical strategy and cost modelling
- Medicare Secondary Payer rules for under-20 employers
- Employee Navigator for eligibility & enrollment
- Creditable coverage notices, sent on schedule
Two honest answers. Different people.
Neither route is the right one for everybody, and anyone who tells you otherwise is selling. A Supplement buys predictability and freedom of choice for a higher monthly premium. An Advantage plan lowers the premium and adds extras, in exchange for a network and an out-of-pocket maximum you may actually reach. Specific plans and premiums vary by county and carrier.
Six windows. Each one does something different.
Most people only know about the fall one, and it is not the one that matters most. These are the windows we track for clients, with the dates that apply nationwide.
Initial Enrollment Period — seven months
Three months before the month you turn 65, that month, and three months after. Enroll in the first three and coverage starts on time. Wait until after and your start date slips, which is how gaps in coverage happen.
Medigap Open Enrollment — six months
Starts the month your Part B begins. Inside it, any Supplement plan sold in your state must take you regardless of health history. Once it closes, in most states carriers can decline you or charge more. This is the single most consequential window in Medicare and the most commonly missed.
Annual Election Period — 15 October to 7 December
The fall window everyone has heard of. Change your Advantage plan, change your Part D plan, or move between Original Medicare and Advantage. Changes take effect 1 January. This is when we re-price every client's drug plan, because formularies change every year.
Medicare Advantage Open Enrollment — 1 January to 31 March
A second chance, but only if you are already in an Advantage plan. You can switch to a different Advantage plan or drop back to Original Medicare and add a drug plan. One change only. Useful when a January doctor visit reveals a network problem.
Special Enrollment Periods — when life changes
Leaving an employer plan, moving out of a plan's service area, losing retiree coverage, a carrier exiting the market, qualifying for Extra Help. Each opens its own window with its own length. Tell us what changed and we will tell you what you are entitled to.
General Enrollment Period — 1 January to 31 March
The catch-up window for people who missed Part B entirely. Coverage now starts the month after you enroll, which is an improvement — but the late-enrollment penalty still attaches, and it is permanent. Do not plan to use this one.
Medicare does not send a reminder. The penalty is quiet, permanent, and it starts the month you were supposed to act.
What Medicare actually costs this year.
These are the published 2026 amounts from the Centers for Medicare & Medicaid Services. They change every January, and two of them — IRMAA and the Part D penalty — are the ones that surprise people, because neither appears on any plan brochure.
Your own number depends on your income two years ago, whether you had creditable drug coverage, and which plan you choose. We will work it out with you before you enroll rather than after.
Part B: $202.90 a month, $283 deductible
The standard 2026 premium, up from $185.00 in 2025. The annual deductible rose to $283. After that Medicare pays 80% of approved charges and you pay the rest, with no annual ceiling on your share.
Part A: $1,736 per benefit period
Then $434 a day for hospital days 61 to 90, and $217 a day for skilled nursing days 21 to 100. Free premium for most people, but the cost sharing is real — and a benefit period can restart within the same calendar year.
Part D: $2,100 out-of-pocket cap
The hard annual ceiling on what you pay for covered drugs, and the most significant improvement to Medicare in years. Plan deductibles can run up to $615 in 2026, and premiums vary widely by plan — which is why the cheapest premium is often not the cheapest year. See Part D plan selection.
IRMAA: the surcharge above $109,000
Single filers over $109,000 and joint filers over $218,000 pay more for both Part B and Part D — Part B running from $284.10 up to $689.90 a month, plus $14.50 to $91.00 on Part D. It is based on your tax return from two years ago, so a one-off event like selling a property can trigger it. A life-changing event can be appealed on form SSA-44. How IRMAA works.
The penalties, which never go away
Part B adds 10% for every full year you could have enrolled and did not, for as long as you have Medicare. Part D adds 1% of the national base premium for each month without creditable drug coverage, also permanently. Both are avoidable with a phone call at the right time. Our free Part D Penalty Calculator shows you the arithmetic.
The case where Medicare and a group plan overlap.
This is where being a group health agency first matters. We already administer employer plans across the Northeast, so when an employee or an owner turns 65 we are looking at both sides of the question at once — the group plan and Medicare — instead of guessing at whichever half we cannot see.
Employers: this is a compliance exposure, not just an employee favour. Getting Medicare Secondary Payer rules or creditable coverage notices wrong creates real liability. See our employer Medicare page.
Employer size changes the answer completely
At 20 or more employees the group plan generally pays first and you can usually delay Part B without penalty. Below 20, Medicare typically pays first — and delaying Part B can leave you with almost no coverage while you believe you are insured. Check the headcount before deciding anything.
HSA contributions have to stop
You cannot contribute to a Health Savings Account once any part of Medicare starts, and Part A can backdate up to six months. Owners and employees who contribute all year and enroll mid-year regularly end up with an excess contribution to unwind. Plan the stop date before you file.
Creditable coverage is a document, not an assumption
Your employer plan's drug coverage either is creditable or it is not, and the plan has to tell you in writing each year. That letter is what protects you from the Part D penalty later. We make sure our group clients issue them, and we keep copies for the individuals we advise.
Leaving the group plan opens a window
Retiring or dropping employer coverage triggers a Special Enrollment Period for Part B and Part D, and a guaranteed-issue right for a Supplement in many cases — but the clock is short and it starts sooner than most people expect. Call us the month you know the date, not the month after.
Rooted in the Northeast. Serving clients nationwide.
Medicare is federal, but the plans are not. Advantage networks and Supplement pricing are decided county by county, and Massachusetts, New York and Connecticut each write their own Medigap rules on top. Knowing which hospital system a plan actually contracts with is local knowledge, and it is the knowledge that decides whether a plan works for you.
Our home ground runs from Boston and Andover through Worcester, the North and South Shores, the Cape and Western Massachusetts, down through Connecticut, New York City and all five boroughs, Long Island, New Jersey and Philadelphia, plus New Hampshire and Maine. Beyond it we serve clients in all 50 states, directly where we are licensed and through trusted affiliates elsewhere.
Independent, and not owned by a carrier
There is no house plan we are expected to place. AHIP-certified and recertified every year, NAHU-accredited, multi-state licensed. More about the agency on our about page.
No fee, ever, for Medicare help
Carriers pay a commission that is set by CMS and identical whichever plan you choose through us. Your premium is the same whether you enroll on your own or with a broker — so there is no version of this where using us costs you money.
Tech-forward, on the employer side too
For our group clients, eligibility, enrollment and compliance tracking run through Employee Navigator — provided at no cost to eligible groups, with AI-assisted plan building and 600+ carrier, payroll and TPA integrations. Employee Navigator acquired Ease in 2023, and through 2026 we are moving every client onto the modern portal.
The whole household, not just the Medicare piece
A spouse still under 65 needs individual coverage. A consultant working past retirement needs a self-employed plan. Snowbirds need to know what travels. We handle all of it from one file.
Go deeper on any of these.
Four detail pages, one per decision. Each one goes further than this overview does — and if you would rather just ask, call (800) 779-4090.
Medicare Supplement & Advantage
Medigap Plan G, Plan N and high-deductible G alongside Advantage HMO, PPO and Special Needs Plans — with the network and underwriting rules that decide between them.
Part D Drug Plans
How formularies, tiers and pharmacy networks change what you actually pay — and why we price your specific prescription list through every plan rather than sorting by premium.
Part D Cost & IRMAA
The income adjustment above $109,000, the late-enrollment penalty that never expires, and the SSA-44 appeal that gets an IRMAA surcharge reversed after a life-changing event.
Group Medicare for Retirees
For employers: group Supplement and group Advantage arrangements, retiree cost modelling, and the Medicare Secondary Payer rules that change with your headcount.
Tell us where you are in the process.
Turning 65, already enrolled and unhappy, or helping a parent — all three are normal calls. Complete the form and a licensed agent will be in touch, or call and we will look at it together on the phone. There is no cost and no obligation.
We do not offer every plan available in your area. Currently we represent [NN] organizations which offer [NN] products in your area. Please contact Medicare.gov, 1‑800‑MEDICARE, or your local State Health Insurance Assistance Program to get information on all of your options. This page is general educational information, not legal, tax or insurance advice for your particular situation.