Connecticut Insurance Guide

Turning 65 and Still Working in Connecticut (2026 Guide)

⚡ Key Takeaways
  • If your Connecticut employer has 20 or more employees, the group health plan generally pays primary and Medicare pays secondary, which is what makes it safe to delay Part B while you keep working.
  • If your employer has fewer than 20 employees, Medicare generally becomes primary at 65 — and skipping Part B can leave you functionally uninsured for the majority of your medical bills even though you are still paying group premiums.
  • Most people who are still working take premium-free Part A at 65, but you must stop HSA contributions roughly six months before you enroll in Medicare or claim Social Security because Part A can be backdated up to six months.
  • When active employment or the group coverage ends, you generally get an 8-month Special Enrollment Period to take Part B without a late penalty — and COBRA and retiree coverage do not extend that clock.
  • The Part B late-enrollment penalty is commonly described as 10% of the standard premium for each full 12-month period you were eligible but not enrolled, and it generally lasts as long as you have Part B.
  • Connecticut requires Medicare Supplement (Medigap) plans to be offered on a continuous, year-round guaranteed-issue basis, so a CT resident who leaves an employer plan at 67 or 70 is in a far better position than someone in most other states.
Direct answer

If you are turning 65 in Connecticut and still working, the deciding question is your employer’s size. At 20 or more employees, the group plan usually pays primary, so you can generally delay Part B penalty-free and enroll later using the 8-month Special Enrollment Period. Under 20 employees, Medicare usually pays primary, and delaying Part B can be financially catastrophic. Most people still take premium-free Part A unless they are contributing to an HSA. Because Connecticut sells Medigap on a year-round guaranteed-issue basis, a later transition is unusually forgiving here — but confirm the details with your plan administrator, a licensed Connecticut broker, or free CHOICES counseling before you decide.

Turning 65 While Still Working in Connecticut: What Actually Happens

A generation ago, 65 and retirement were the same date. In Connecticut today they very often are not. Plenty of people in Hartford, Stamford, New Haven, and Danbury turn 65 while running a department, billing clients, teaching, or holding a shift they have no intention of giving up. Health coverage is one of the main reasons they keep working — and that is exactly why the Medicare decision at 65 is more complicated for them than for someone who is retiring cleanly on their birthday.

Here is what actually happens. About three months before the month you turn 65, your Initial Enrollment Period opens. It runs seven months total: the three months before your birthday month, your birthday month, and the three months after. If you are already collecting Social Security or Railroad Retirement benefits, you will typically be enrolled in Parts A and B automatically and a red-white-and-blue card will arrive in the mail. If you are not collecting benefits yet — which describes most people still working full time — nothing happens automatically. No one from Medicare calls you. No one from your employer is required to tell you what to do. The window opens, and it closes, and the consequences of getting it wrong are permanent.

What you should not do is assume that “I have good insurance through work” is a complete answer. Sometimes it is. Sometimes it is the most expensive assumption a Connecticut worker will ever make. The difference comes down to a handful of federal rules, most of which turn on one number: how many people your employer employs.

Because so much of this depends on timing, it helps to read this alongside our overview of how the Medicare Initial Enrollment Period works in Connecticut, which walks through the seven-month window in detail.

The 20-Employee Rule: Who Pays First and Why It Decides Everything

Medicare’s coordination-of-benefits rules determine which plan is the “primary payer” — the one that pays first — and which is “secondary,” paying some or all of what the primary leaves behind. When you are 65 or older and covered by a group health plan through your own current employment or your spouse’s current employment, the rule generally works like this:

20 or more employees. The group health plan is generally the primary payer, and Medicare is secondary. Federal law prohibits an employer of this size from pushing Medicare-eligible workers off the group plan or offering them a worse deal because of age. In practical terms, this is the situation where delaying Part B is normally safe: your group plan is still paying your claims first, exactly as it did at 64.

Fewer than 20 employees. Medicare generally becomes the primary payer once you are eligible at 65, and the small-group plan pays secondary. This is the trap. If Medicare is primary and you did not enroll in Part B, the group plan can pay as though Medicare had already paid its share — which means a large portion of your outpatient, physician, lab, imaging, and surgical bills may simply go unpaid. You are still writing a premium check every month. You are still handing over an insurance card. And you may still be exposed to tens of thousands of dollars of liability on a single hospitalization.

Connecticut has a very large number of small employers: family practices, independent pharmacies, machine shops in Waterbury and New Britain, restaurants, small law and accounting firms, nonprofits, contractors. If you work for one of them — or your spouse does and you are on their plan — the under-20 rule is not an edge case. It is your case.

Two clarifications that trip people up. First, the count is generally based on employees, not on how many people are enrolled in the health plan. Second, “current employment” matters: retiree coverage and COBRA are not current employment coverage, so they do not protect your Part B delay even if the employer is large. We cover that distinction in depth in our guide to COBRA versus Medicare at 65 in Connecticut.

How the Rules Work (Federal Rules, Connecticut Choices)

It is worth separating two layers that people constantly blend together. The enrollment rules — Part A, Part B, penalties, Special Enrollment Periods, the 20-employee threshold, IRMAA, the HSA lookback — are federal. They are identical in Greenwich and in Torrington and in Tulsa. Nobody in Connecticut gets a different penalty formula.

What is local is everything about the plan you actually buy when you leave the employer plan. Which hospitals and specialists are in a Medicare Advantage network in Fairfield County versus Windham County. Whether your Yale New Haven Health or Hartford HealthCare physicians participate. Which Medigap plan letters are competitively priced in your ZIP code. Which Part D formulary covers your exact drug list at a pharmacy you can reach. And, uniquely for Connecticut residents, the state’s own Medigap rules — which we will get to shortly and which meaningfully change the risk calculation for someone delaying Medicare into their late sixties or seventies.

So the honest framing is: the federal rules tell you when you must act, and Connecticut’s market tells you what to buy when you do. Getting the first part wrong creates a permanent penalty. Getting the second part wrong creates an annual annoyance you can usually fix later — especially here.

Should You Take Part A at 65? The Premium-Free Default and the HSA Conflict

Part A covers inpatient hospital care, skilled nursing facility care after a qualifying stay, some home health, and hospice. If you or your spouse worked and paid Medicare payroll taxes for roughly ten years — 40 quarters — Part A costs you nothing in premium. For that reason, the standard advice for someone still working is: take premium-free Part A at 65. It layers behind your employer plan and can pick up some hospital cost-sharing at no additional monthly cost.

There is one large exception, and it catches a lot of Connecticut professionals: the health savings account.

You cannot contribute to an HSA for any month in which you are enrolled in any part of Medicare, including premium-free Part A. Worse, Part A enrollment can be made retroactive up to six months (but never earlier than the first month you were eligible) when you enroll after your Initial Enrollment Period or when you claim Social Security. That retroactivity is what generates the surprise: someone signs up in November, Part A is backdated to May, and every HSA contribution made from May forward is now an excess contribution subject to tax and potential penalty.

The practical rule most advisors use: if you intend to keep contributing to an HSA past 65, do not enroll in Part A, and stop HSA contributions at least six months before the month you plan to enroll in Medicare or file for Social Security. Note that your employer’s contributions to your HSA count too, so this is a conversation to have with payroll, not just with yourself. IRS Publication 969 is the governing document, and this is genuinely worth reviewing with a tax professional. For the full walk-through, see our guide on HSA contributions and Medicare at 65 in Connecticut.

One more nuance: if you are already receiving Social Security benefits, you generally cannot decline Part A without withdrawing from Social Security and repaying benefits received. If HSA contributions matter to you, delay Social Security as well.

When Delaying Part B Is Safe — and When It Creates a Lifelong Penalty

Part B covers outpatient and physician services, and unlike Part A it carries a monthly premium for essentially everyone. That premium is why people delay it — and why delaying it incorrectly is so expensive.

Delaying Part B is generally safe when: you (or your spouse, if you are covered as a dependent) are actively working, the coverage comes from that current employment, and the employer has 20 or more employees. In that situation you are considered to have coverage that lets you use a Special Enrollment Period later.

Delaying Part B is generally not safe when: the employer has fewer than 20 employees; the coverage is COBRA; the coverage is retiree coverage from a former employer; the coverage is an individual plan bought through Access Health CT; the coverage is TRICARE without the required Medicare enrollment; or you are covered as a domestic partner rather than a spouse under a plan whose rules do not extend the protection. Several of these look and feel like “real insurance” and still fail the test.

The penalty itself is commonly described as an additional 10% of the standard Part B premium for each full 12-month period you were eligible for Part B and did not enroll while lacking qualifying coverage. It is added to your premium and it generally lasts for as long as you have Part B — which for most people means for life. Someone who delays four years without protection can face a surcharge in the neighborhood of 40% permanently. Do not try to calculate a 2026 dollar figure from an article; verify the current standard premium at Medicare.gov and get your specific situation confirmed. Our dedicated breakdown of the Part B late-enrollment penalty for Connecticut residents goes through the arithmetic and the limited appeal options.

Part D has its own, separate late-enrollment penalty, calculated from the number of months you went without creditable prescription drug coverage. Most large employer drug plans are creditable, but you should receive an annual notice saying so — keep it. If your employer plan’s drug coverage is not creditable, you may need a standalone Part D plan even while still working.

The 8-Month Special Enrollment Period After Work Coverage Ends

This is the safety valve, and it is narrower than people think.

When your current-employment group health coverage ends — or the employment itself ends, whichever comes first — you generally get an 8-month Special Enrollment Period to enroll in Part B without a late penalty. There is also a shorter window, commonly described as 63 days, to pick up Part D creditable drug coverage without a penalty. Those two clocks are different lengths and they start at roughly the same time, which is precisely why people miss the Part D one.

Three things about the 8 months that cost Connecticut retirees real money:

It does not restart for COBRA. If you retire in March and elect 18 months of COBRA, your 8-month Part B window still started in March. Ride COBRA to its end and you have blown through the SEP by ten months and are looking at a permanent penalty plus a gap in coverage. COBRA is generally not creditable coverage for Part B purposes. This single mistake is one of the most common expensive errors in Medicare.

It does not restart for retiree coverage. A retiree medical plan from a Connecticut municipality, hospital system, or large employer is a benefit, not current employment coverage. The clock runs.

Coverage does not begin the day you sign up. Part B effective dates follow their own schedule. If you want Medicare to start the first of the month after your group plan ends, you generally need to file before that date — not after. Plan on starting the paperwork 60 to 90 days ahead of your last day of coverage, not on your last day.

To use the SEP you will typically need Form CMS-40B (Application for Enrollment in Part B) and Form CMS-L564 (Request for Employment Information), which your employer or plan administrator completes to prove you had qualifying group coverage. More on that in the HR section below. If you want the general filing mechanics, see how to apply for Medicare in Connecticut.

Connecticut’s Medigap Advantage: Year-Round Guaranteed Issue

Here is where Connecticut residents get a genuine, meaningful break that most Americans do not.

Under federal rules, your one protected shot at a Medicare Supplement plan is the 6-month Medigap Open Enrollment Period that starts when you are 65 or older and enrolled in Part B. Miss it in most states and an insurer can medically underwrite you — ask about your diabetes, your cardiac history, your cancer history — and decline you or charge more. That is why “delay Part B until 70, then buy a Medigap” is risky advice in most of the country.

Connecticut is different. Connecticut is one of a small number of states — New York is the other most often cited — that requires Medicare Supplement policies to be offered on a continuous, year-round guaranteed-issue basis. In practice, a Connecticut resident enrolled in Medicare Parts A and B can generally apply for or switch a Medigap plan at any time of year without medical underwriting, regardless of health history.

What that means for a worker delaying Medicare: the worst-case outcome of a mistimed Medigap decision in Connecticut is considerably softer than in Florida or Texas. If you work to 68, leave the employer plan, and enroll in Part B through your SEP, you should be able to buy a Medigap plan on a guaranteed-issue basis rather than getting underwritten out of the market.

Three honest caveats, because this benefit gets oversold. First, guaranteed issue governs acceptance, not price — premiums still vary by carrier, plan letter, age, and area, sometimes substantially, so shopping still matters a great deal. Second, the protection generally applies to Medigap, not to Medicare Advantage or Part D, which run on their own enrollment calendars. Third, you still need to be enrolled in Part B for a Medigap plan to function, so the Part B penalty risk is untouched by this rule. Connecticut’s Medigap rule is a strong safety net for the plan decision, not for the enrollment decision. For the plan-side detail, see our guides to Medicare Supplement plans in Connecticut and the Medigap open enrollment window at 65. Always confirm current rules with the Connecticut Insurance Department.

Deadlines, Windows & Penalties: The Full Timeline

Written as a sequence, here is every clock that can run against a Connecticut worker turning 65:

Initial Enrollment Period — 7 months. Three months before your birthday month, your birthday month, three months after. This is your window for Part A, Part B, and initial drug coverage if you are not delaying. Enrolling in the three months before your birthday month generally gives you the earliest start date.

Special Enrollment Period for Part B — 8 months. Begins when current-employment coverage or the employment ends. Does not reset for COBRA or retiree coverage.

Special Enrollment Period for Part D — commonly 63 days. Much shorter. Losing creditable drug coverage starts a fast clock.

Medigap Open Enrollment — 6 months federally. Starts when you are 65+ and enrolled in Part B. In Connecticut, the practical stakes are reduced by year-round guaranteed issue, but the federal window still exists.

General Enrollment Period — January 1 to March 31. The fallback if you miss everything. Coverage now generally starts the first of the month after you enroll, and the late penalty typically applies.

Annual Enrollment Period — October 15 to December 7. For changing Medicare Advantage and Part D plans for the following year.

HSA six-month lookback. Not a Medicare deadline exactly, but a hard tax boundary. Stop contributions six months before enrollment.

Our full calendar of Connecticut Medicare enrollment deadlines for 2026 lays these out side by side.

What It Costs in 2026: Comparing the Employer Plan Against Medicare

The question that actually decides whether you stay on the employer plan is not “which is cheaper on paper” — it is “what is my true total annual cost, including my spouse and my prescriptions, under each option.”

To do this honestly, build two columns. On the employer side: your payroll deduction for the year, the deductible, the out-of-pocket maximum, and — critically — whether your spouse and any dependents can stay on the plan if you leave it, and what their cost becomes. Many people discover the employer plan is a bargain only because it also covers a spouse; a single subscriber’s rate can look very different.

On the Medicare side: the Part B premium (plus any IRMAA surcharge), a Medigap premium if you choose that route, a Part D premium, and your expected drug costs. Note that Medicare Advantage plans can carry a low or zero additional premium but substitute network limits, prior authorization, and copays.

Two 2026-specific facts belong in this math. First, Part D now has an annual out-of-pocket cap of $2,000 under the Inflation Reduction Act, indexed going forward — a structural improvement for anyone on expensive medications, and one that has changed the calculus for people who stayed on employer plans purely for drug coverage. Second, the Medicare Prescription Payment Plan allows you to spread out-of-pocket drug costs into monthly payments across the year rather than absorbing a large January hit. Our overview of the Part D IRA changes in Connecticut covers both.

Third factor: IRMAA. If you are still working, you are probably still earning, and Part B and Part D surcharges are based on a two-year income lookback. A high-earning Norwalk or Greenwich professional may face a surcharge based on income from two years prior. If your income dropped because of retirement, work reduction, or a life-changing event, file Form SSA-44 to request that Social Security use current income instead. This is a routine, winnable request that many people never make.

Item / Scenario What to Expect in 2026 What Changes It
Part A while still working Typically $0 premium with 40 quarters of Medicare-taxed work; commonly taken as secondary coverage HSA contributions — if you contribute, delaying Part A is usually the right call
Part B premium A standard monthly premium set annually by CMS; verify the current figure at Medicare.gov IRMAA surcharges based on a 2-year income lookback; SSA-44 appeal for life-changing events
Part B late penalty Commonly 10% of the standard premium per full 12-month period without qualifying coverage, generally for life Whether your employer had 20+ employees; whether coverage was COBRA or retiree coverage
Medigap in Connecticut Monthly premium varies widely by plan letter, carrier, age, and area — but issued year-round on a guaranteed-issue basis Plan letter chosen, carrier rating method, county, tobacco status; shopping still matters
Part D drug costs Plan premium plus cost-sharing, with a $2,000 annual out-of-pocket cap under the Inflation Reduction Act Your specific drug list, formulary tier placement, pharmacy choice, IRMAA surcharge
Staying on the employer plan Your payroll deduction plus deductible and out-of-pocket maximum — sometimes competitive, sometimes far worse Employer size, whether a spouse or dependents are covered, whether drug coverage is creditable

Illustrative only — 2026 figures change annually and vary by plan and county. Verify current amounts at Medicare.gov and confirm with a licensed Connecticut broker.

For a fuller cost picture, see how much Medicare costs at 65 in Connecticut. And if your income is modest, do not skip the Connecticut Medicare Savings Programs — QMB, SLMB, and ALMB — administered by the CT Department of Social Services. These can help pay the Part B premium and some cost-sharing, and Connecticut’s income limits have historically been comparatively generous. The limits change annually, so check current figures directly with CT DSS rather than relying on any article.

Small-Employer Traps Common at Connecticut Businesses

Connecticut’s economy runs heavily on small and mid-size employers, and a specific cluster of problems shows up again and again at businesses under the 20-employee line.

Nobody at the company knows the rule. At a 12-person firm there is often no benefits department — there is an office manager and a broker who visits once a year. The employee assumes the plan works the same at 65 as at 64. It may not.

The carrier assumes you enrolled in Medicare. Small-group plans frequently pay claims as secondary once you turn 65, whether or not you actually have Part B. You will discover this from an explanation of benefits after a procedure, which is the worst possible time.

Headcount is near the threshold. A company that had 22 employees last year and 18 this year can flip your primary/secondary status. The rule generally looks at employer size over a specified period, and seasonal Connecticut businesses — landscaping, marine, hospitality along the shoreline — can cross the line in both directions. Get the determination in writing.

You are on a spouse’s small-group plan. The employer-size test attaches to the employer providing the coverage, not to you. Your spouse’s 9-person accounting practice in Middletown makes Medicare primary for you at 65.

The plan is a level-funded, association, or ICHRA arrangement. These have grown quickly among Connecticut small employers and their interaction with Medicare is not intuitive. An individual coverage HRA in particular is not group health coverage in the classic sense, and it can affect both your Part B delay protection and your eligibility to use it. Ask specifically.

Owners and partners. If you are a self-employed Connecticut business owner covering yourself through a small-group or individual plan, the 20-employee protection likely does not apply to you at all.

None of these is exotic. Every one of them is common, and every one of them produces the same outcome — a person who paid premiums all year and still got a bill they cannot pay. Our roundup of Medicare enrollment mistakes in Connecticut covers several more.

What to Hand HR — and What to Ask For in Writing

Do not walk into HR with “what should I do about Medicare?” They are usually not permitted to advise you, and if they guess wrong you carry the consequence. Walk in with specific factual questions and ask for written answers.

Ask for these five facts in writing:

1. How many employees does the company employ for purposes of Medicare secondary payer rules — 20 or more, or fewer than 20? Ask for a yes/no on whether the plan pays primary to Medicare for active employees age 65+.

2. Is the prescription drug coverage creditable for Medicare Part D purposes? Ask for the annual Creditable Coverage Notice and save it. You may need it years later to avoid a Part D penalty.

3. What happens to my spouse and dependents if I drop the plan, and what is the single-subscriber rate versus the family rate?

4. What is my exact last day of active coverage if I retire on a given date — the last day worked, the end of that month, or something else? This date starts your 8-month clock.

5. Will you complete Form CMS-L564? This is the Request for Employment Information that Social Security uses to verify you had qualifying group coverage. Ask early. Chasing a signature from a former employer months later — or from a company that has since been acquired, which happens constantly in Connecticut — is a real risk. If the employer is gone or unresponsive, ask Social Security about alternative proof such as pay stubs or plan documents.

Hand HR nothing sensitive and sign nothing that waives coverage until you have confirmed what replaces it and on what date. And if HR tells you that you “have to” go on Medicare at 65 while you are still actively working at an employer with 20 or more employees, that instruction is generally improper — get it in writing and get a second opinion.

Connecticut County & Network Differences

Once you do leave the employer plan, geography starts to matter. Connecticut’s eight counties — Fairfield, Hartford, Litchfield, Middlesex, New Haven, New London, Tolland, and Windham — do not offer identical Medicare markets.

Medicare Advantage plan availability, benefits, and networks are set at the county level. A plan that looks excellent in Hartford County may have a thinner specialist network in Litchfield or Windham, where population density is lower and provider options are more limited. Someone in Stamford or Greenwich may also be crossing into New York for care, which raises network questions a Torrington resident never faces.

Network membership is the concrete question. Do your physicians participate with the plan you are considering — at Yale New Haven Health, Hartford HealthCare, Trinity Health Of New England, Nuvance Health, or UConn Health? Health system participation in Medicare Advantage networks changes, sometimes mid-year and sometimes contentiously. Verify current participation directly with the plan and with your physician’s office before enrolling, not from a directory screenshot.

Medigap is the counterweight here: a Medicare Supplement plan generally works with any provider nationwide that accepts Medicare, which is why Connecticut residents who travel, who winter in Florida, or who see specialists across state lines often gravitate to it — and why Connecticut’s year-round guaranteed issue makes that route unusually accessible. The structural tradeoff is laid out in Medicare Advantage vs. Supplement in Connecticut.

Three Connecticut Scenarios

The following are hypothetical illustrations, not real clients, and not a prediction of your result.

Scenario 1 — Large employer, West Hartford, age 65. A project manager at a 400-employee company turns 65 and plans to work until 68. Her group plan pays primary. She enrolls in premium-free Part A only, keeps her employer coverage, declines Part B, and files her employer’s creditable coverage notice each year. She stops HSA contributions before enrolling in Part A. At 68 she uses her 8-month SEP, enrolls in Part B, and — because she lives in Connecticut — buys a Medigap plan on a guaranteed-issue basis without underwriting. No penalty, no gap.

Scenario 2 — Small employer, Waterbury, age 65. A machinist at an 11-person shop assumes his plan is fine. It is not: with fewer than 20 employees, Medicare is primary at 65. He does not enroll in Part B. Eight months later he has outpatient surgery, and the group plan pays as secondary to a Medicare Part B that does not exist. He is left with a large balance and must wait for the General Enrollment Period to get Part B — with a late penalty attached. Had someone asked HR one question at 64, none of this happens.

Scenario 3 — Retiring at 66 in Milford, with COBRA on the table. A retiring supervisor is offered 18 months of COBRA and takes it because the network is familiar. His 8-month Part B SEP started the day his active coverage ended, not the day COBRA ended. He rides COBRA for 18 months and enrolls in Part B in the next General Enrollment Period, with a permanent penalty and a coverage gap. In the alternate version, he enrolls in Part B effective the month after active coverage ends, adds a Connecticut Medigap plan and a Part D plan, and uses COBRA only if it is genuinely needed for a spouse.

If your spouse is under 65, that adds a second layer — see Medicare at 65 when your spouse is under 65 in Connecticut, since Access Health CT may become part of the plan.

Common Mistakes That Cost Connecticut Retirees

Assuming employer size does not matter. It is the single most consequential fact in this entire article.

Treating COBRA as a bridge to Medicare. It is not creditable coverage for Part B and it does not extend your SEP.

Contributing to an HSA after enrolling in Part A. Or enrolling in Part A without realizing it will be backdated six months.

Missing the Part D clock while watching the Part B clock. Different lengths, same start.

Waiting until the last day of coverage to file. Effective dates are not same-day. Start 60 to 90 days out.

Never asking for the creditable coverage notice. You may need it years later and the employer may be gone.

Assuming a spouse’s small-group plan protects you. The employer-size test follows the employer providing coverage.

Assuming Connecticut’s Medigap rule fixes an enrollment mistake. It protects your plan choice, not your Part B timing.

Not appealing IRMAA after retiring. If your income dropped, SSA-44 exists for exactly that reason.

Buying from whoever called first. Unsolicited Medicare calls are a well-documented problem. Choose your advisor; do not let them choose you.

Your Step-by-Step Connecticut Action Plan

At 64 years, 6 months: Ask HR, in writing, whether the employer has 20 or more employees and whether the plan pays primary for active employees 65 and over. Request the creditable coverage notice for drugs.

At 64 years, 6 months (if you have an HSA): Decide whether you will keep contributing. If you will enroll in Medicare or claim Social Security, stop contributions six months before that date and confirm employer contributions stop too.

Three months before your birthday month: Your Initial Enrollment Period opens. If the employer is under 20 employees, enroll in Parts A and B now. If 20 or more, enroll in Part A only (unless HSA), and document your decision.

If you are already on Social Security: Watch for automatic enrollment and your card. Understand what you are keeping or declining before you act.

Each year you keep working: Re-confirm employer size and re-file the creditable coverage notice. Small companies change size.

60 to 90 days before your coverage ends: Start the SEP paperwork — CMS-40B plus CMS-L564 signed by the employer. Target a Part B effective date with no gap.

At the same time: Compare Medigap versus Medicare Advantage for your Connecticut county, run your exact drug list through the Medicare Plan Finder for Part D, and confirm your physicians’ network status directly.

If income is limited: Check Connecticut Medicare Savings Program eligibility with CT DSS, and HUSKY Health if you may be dual-eligible.

After you retire: If your income dropped, file SSA-44 to challenge an IRMAA surcharge based on your old income.

A condensed version lives in our turning 65 Medicare checklist for Connecticut.

Where a Licensed Connecticut Broker (and CHOICES) Fits

Two free resources exist, and using both is the most reliable way to avoid a permanent mistake.

CHOICES is Connecticut’s State Health Insurance Assistance Program, delivered through the Department of Aging and Disability Services and the Area Agencies on Aging. Counselors are trained volunteers and staff who do not sell anything and receive no commission. They are an excellent, genuinely unbiased second opinion — especially on enrollment timing, penalties, and Medicare Savings Program eligibility.

An independent, licensed Connecticut broker covers the other half: which specific plans exist in your county, how your physicians and drugs actually map onto them, and how to execute the paperwork on the right dates. A broker is compensated by the carriers, so there is no cost to you for the guidance, and plan premiums are set by the carrier and filed with regulators — you do not pay more for using a broker than for enrolling yourself.

We Find Your Insurance LLC is an independent brokerage headquartered in Farmington, Connecticut, working with residents across all eight counties. We do not guarantee savings, approval, or any particular plan outcome — nobody legitimately can. What we do is make sure the employer-size question gets answered before it becomes a claim, that the 8-month clock does not quietly expire, and that Connecticut’s year-round Medigap guaranteed issue actually gets used to your advantage. If you would like a starting point on choosing anyone at all, see how to choose a Medicare agent in Connecticut.

Whatever you do, do not make this decision from a mailer. Get the employer-size answer in writing, verify current figures at Medicare.gov, and get a second set of eyes on the dates.

Sources & References

  1. Medicare.gov — Get Started with Medicare (enrollment timing and when to sign up)
  2. Medicare.gov — Official U.S. Government Medicare Site (current premiums and deductibles)
  3. Social Security Administration — Medicare Enrollment and Applications
  4. Social Security Administration — Form SSA-44, Medicare IRMAA Life-Changing Event
  5. Centers for Medicare & Medicaid Services — Coordination of Benefits and Medicare Secondary Payer Rules
  6. IRS — Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans
  7. Connecticut Department of Aging and Disability Services — CHOICES Medicare Counseling
  8. Connecticut Insurance Department — Medicare Supplement Rules and Rate Filings
  9. Connecticut Department of Social Services — Medicare Savings Programs and HUSKY Health

Frequently Asked Questions

Do I have to enroll in Medicare at 65 if I am still working in Connecticut?
Not necessarily. If your employer has 20 or more employees and you are covered through that current employment, the group plan generally pays primary and you can usually delay Part B without penalty. If the employer has fewer than 20 employees, Medicare generally becomes primary at 65, and delaying Part B can leave most of your outpatient bills unpaid. Confirm your employer’s size in writing before deciding.
Should I take Part A at 65 while I am still working?
Usually yes, if it is premium-free, because it layers behind your employer plan at no monthly cost. The exception is a health savings account: you cannot contribute to an HSA while enrolled in any part of Medicare, and Part A can be backdated up to six months. If you plan to keep contributing to an HSA, delay Part A and stop contributions six months before you enroll.
How long do I have to sign up for Part B after I stop working?
Generally 8 months from when your current-employment group coverage or the employment ends, whichever comes first. That is your Special Enrollment Period for Part B without a late penalty. Part D has a much shorter window, commonly 63 days. Importantly, neither clock restarts for COBRA or retiree coverage. Start the paperwork 60 to 90 days before your coverage ends to avoid a gap.
Does COBRA count as employer coverage for Medicare purposes?
Generally no. COBRA is not considered coverage based on current employment, so it does not protect you from the Part B late-enrollment penalty and does not extend your 8-month Special Enrollment Period. Your clock starts when active coverage ends, not when COBRA ends. This is one of the most expensive and most common Medicare mistakes, and it is entirely avoidable with one conversation.
Can I still buy a Medigap plan in Connecticut if I delay Medicare until 70?
Generally yes. Connecticut is one of a small number of states requiring Medicare Supplement plans to be sold on a continuous, year-round guaranteed-issue basis, so CT residents can typically apply without medical underwriting regardless of age or health history. Premiums still vary by plan letter, carrier, age, and area, so shopping matters. You must also be enrolled in Part B for a Medigap plan to work.
What paperwork do I need from my Connecticut employer?
Two things matter most. Form CMS-L564, the Request for Employment Information, is completed by your employer to prove you had qualifying group coverage, and it accompanies Form CMS-40B when you enroll in Part B. You should also keep every annual Creditable Coverage Notice for prescription drugs. Request both early — chasing a signature from a former or acquired employer later is a real problem.

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