Medicare Coverage
Original Medicare, Advantage, Supplements and Part D — explained clearly, with a free assessment and yearly plan check-up.
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30+ years helping families protect what matters
Your experts in Medicare, Social Security & Asset Protection
Helping you prepare for — and protect you in — tomorrow. We cut through the confusion with clear, one-on-one guidance so you can make retirement decisions with confidence.
- ★★★★★ Trusted by local retirees & families
- Educate first, plan second
- Independent & local — no call centers
30+ years of guidanceIndependent & local — no call centers
30+Years of experience
50+Years combined expertise
7Ways we protect you
$0Cost for your first consult
Start where you are
Which of these sounds like you?
Most people arrive with one specific worry, not a general interest in insurance. Pick the one that fits and we'll take you straight to the part that matters.
I turn 65 soon
You have a seven-month window around your birthday and a kitchen table covered in mail. Here's what actually has to happen, and when.
Start with Medicare I'm already on MedicareYour plan can move a drug to a higher tier or drop a doctor in January. We re-check the plan you have against the ones we offer every fall.
See how a review works I'm deciding when to claimClaiming at 62 instead of your full retirement age cuts the monthly benefit permanently — and often cuts what your spouse would live on.
Weigh 62 vs. 67 vs. 70 I want income I can't outliveNo pension, a lump sum, and a spreadsheet. We'll talk honestly about what an annuity does well and where it's the wrong tool.
Look at income options I'm protecting my familyIf the paycheck stopped tomorrow, could the mortgage still be paid? We size the number first, then shop it across carriers.
Work out the amount
1-on-1
Real people, real conversations — never a call center
What we do
An old-school approach to modern retirement decisions
Medicare, Social Security and insurance shouldn’t feel overwhelming. We take the time to explain your options in plain language, answer every question, and build a plan that fits your life — then we stay with you year after year.
- Education before enrollment. You’ll understand your choices before you ever sign anything.
- A local office, staffed year-round. When you call, a real person who knows you picks up.
- Independent guidance. We compare options across carriers to fit you — not the other way around.
How we help
Coverage & planning built around your goals
From your first Medicare decision to protecting the assets you’ve worked a lifetime to build — we guide you through all of it.
Social Security Planning
Timing is everything. We help you decide when and how to claim so you maximize your lifetime benefit.
Learn moreLife Insurance
Term and permanent coverage that protects your family’s income, home and future — sized to what you actually need.
Learn moreFinal Expense
Affordable whole-life coverage that spares your loved ones the burden of funeral and end-of-life costs.
Learn moreAccidental Death & Dismemberment
An extra layer of protection that pays a benefit if a covered accident causes serious injury or loss of life.
Learn moreIndexed Universal Life (IUL)
Permanent protection that also builds tax-advantaged cash value you can tap for retirement, with downside protection.
Learn moreAnnuities
Turn a portion of your savings into predictable, guaranteed income you can’t outlive — a paycheck for retirement.
Learn moreNot sure where to start?
Tell us your situation and we’ll point you to the right coverage — no pressure, no cost.
Talk to an Expert
Dates, not pressure
The enrollment windows that actually matter
Four windows do almost all the work. Knowing which one you're in is usually the difference between a clean switch and a penalty you carry for years.
Around your 65th
Initial Enrollment Period
Seven months: the three months before you turn 65, your birthday month, and the three months after. Medicare.gov states it “lasts for 7 months.”
Oct 15 – Dec 7
Medicare Open Enrollment
The one time a year everyone with Medicare can change health and drug plans. The plan must have your request by December 7; coverage starts January 1.
Jan 1 – Mar 31
If you're in an Advantage plan
You can switch to a different Medicare Advantage plan or go back to Original Medicare — and then add a separate drug plan. Coverage starts the first of the month after the plan gets your request.
Nov 1 – Jan 15
Marketplace, if you're under 65
Retired before Medicare starts? Enroll by December 15 for coverage on January 1, or by January 15 for coverage starting February 1.
Sources: Medicare.gov, “Remember Key Medicare Dates” (CMS Product No. 12192, September 2025) and “When does Medicare coverage start?”; HealthCare.gov, “Dates & deadlines.” Retrieved July 31, 2026.
Why TSM Life & Health
Guidance you can trust, service that feels personal
Exceptional customer service isn’t just what we do — it’s who we are. Here’s what that looks like.
Deep expertise
More than 50 years of combined experience in Medicare and Social Security, so you get answers rooted in real knowledge — not guesswork.
Truly responsive service
We make every interaction simple, stress-free and confident. Call our local office and a real person who knows your file will help.
Customized solutions
We listen, understand your priorities, and build a plan that fits your goals and protects what matters most to you and your family.
The TSM process
Four simple steps to peace of mind
01
Reach out
Call or request a free consultation. Tell us where you are and what’s on your mind.
02
We educate
We explain your options in plain language — the pros, the cons and the fine print — until it clicks.
03
We plan together
We build a plan tailored to your goals and budget, then handle the paperwork with you — start to finish.
04
We stay with you
Life changes and so do plans. We review yours every year to make sure it still fits.
Plan year 2026
Real numbers, straight from CMS
We'd rather show you the published figures than a sales pitch. These are Connecticut's 2026 numbers and the national Part B costs everyone pays.
47Medicare Advantage plans in Connecticut for 2026
11Stand-alone Part D drug plans in Connecticut
$283Part B annual deductible for 2026
8States Keith is licensed in
Two 2026 changes worth knowing. The standard Part B premium is $202.90 a month in 2026, up from $185.00 in 2025. And Part D now has a hard ceiling: once you've paid $2,100 out of pocket for covered drugs in 2026, you pay nothing more for them that year.
Sources: CMS, “2026 Medicare Parts A & B Premiums and Deductibles,” released November 14, 2025 — cms.gov/newsroom/fact-sheets/2026-medicare-parts-b-premiums-deductibles. CMS, “Medicare Open Enrollment in Connecticut, 2026” state fact sheet, September 26, 2025. CMS, “Final CY 2026 Part D Redesign Program Instructions,” April 7, 2025. All figures are plan year 2026.
Medicare TPMO Disclaimer: We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP), to get information on all of your options.
TSM Life & Health is a licensed independent insurance agency and is not connected with, affiliated with, or endorsed by the U.S. government, the federal Medicare program, the Social Security Administration, or the Centers for Medicare & Medicaid Services (CMS). Plan availability, benefits, premiums and formularies vary by county and can change each plan year.
No call centers
Just honest, face-to-face advice from people who care
Our promise
We built TSM so no one has to figure this out alone
Our founder watched his own parents navigate Social Security, Medicare and insurance without anyone in their corner. TSM exists so you never feel that same confusion or uncertainty.
- Face-to-face meetings and straightforward answers
- We answer our own phones — never an offshore agent
- Continuous support, not a one-and-done sale
Areas we serve
Licensed in eight states, at home in Connecticut
Our office is on New Haven Avenue in Milford. We work across all eight Connecticut counties and in seven other states — including the ones people retire to.
CTConnecticut
AZArizona
DEDelaware
DCWashington, D.C.
FLFlorida
MAMassachusetts
NCNorth Carolina
VAVirginia
All eight Connecticut counties
In their words
Neighbors who found clarity with TSM
★★★★★
“I was completely lost about Medicare. They sat with me, explained every option and never rushed me. I finally understood what I was signing up for.”
★★★★★
“They walked us through claiming Social Security at 64 versus waiting, and showed us what each choice would leave me if Jim goes first. Nobody had ever explained that part to us.”
★★★★★
“Honest, patient and genuinely kind. When I call, a real person who knows me answers. That’s rare these days.”
Good questions
Answers before you commit
No. Your first consultation — including a Medicare assessment — is completely free and there’s no obligation. We’d rather you feel informed than pressured.
Most people can review and change coverage during the Annual Enrollment Period each fall, and some qualify for Special Enrollment Periods after certain life events. We’ll help you understand which windows apply to you.
Our guidance is provided at no direct cost to you. As an independent agency, we’re compensated by the carriers when you enroll — which means our advice stays focused on finding the right fit for your needs.
Ideally a few years before you plan to claim. The age you file can significantly change your monthly benefit for life, so it pays to run the numbers early and coordinate it with the rest of your retirement income.
Whatever is comfortable for you. We’re happy to meet face-to-face, talk over the phone, or connect virtually — you choose.
Let’s talk
Ready to prepare and protect your tomorrow?
Book a free, no-pressure consultation. We’ll answer your questions and help you take the next step with confidence.