Take the 2-Minute Assessment ↓
Which best describes your health coverage right now?
This is the single most important question — the rules change completely depending on why you have employer-based coverage.
How many employees does the company have?
This determines whether Medicare or the employer plan pays first — and whether you're allowed to delay Medicare without penalty.
What's the annual deductible on that plan?
The amount you pay out of pocket before the plan starts paying its share.
Are you actively contributing to an HSA?
Once you enroll in any part of Medicare, HSA contributions must stop — and getting the timing wrong can trigger tax penalties.
Does anyone else rely on your employer plan?
Medicare only covers you as an individual. If a spouse or dependent is on your plan, leaving it affects them too.
Has the employer told you the drug coverage is "creditable"?
Employers are required to send a notice each year. If the drug coverage is not creditable, delaying Medicare drug coverage builds a permanent late-enrollment penalty.
How would you describe your healthcare needs?
This helps weigh networks, out-of-pocket exposure, and how much flexibility matters to you.
Last one: is your household income above roughly $200,000 (married) or $100,000 (single)?
Higher incomes pay an extra surcharge on Medicare premiums (called IRMAA) — sometimes it's smart to time enrollment around it.
How long ago did the active employment end?
There's a strict 8-month window for enrolling in Medicare after active employment ends — COBRA and retiree coverage do not extend it.
Do you know if the drug coverage is "creditable"?
If it's not, every month without Medicare drug coverage adds to a permanent penalty.
What are you paying each month for this coverage?
COBRA and retiree plans often cost far more than people expect once the employer stops contributing.
Where should I send your personalized read?
Enter your details and your result appears instantly on the next screen. I'll also send a short follow-up with the specific items to verify for your situation.
Your information is only used by Eligry LLC to deliver your result and follow up personally. No spam, no lists sold — ever. Submitting this form does not enroll you in any plan.
Medicare isn't just the better choice for you — it's likely required.
Because the employer has fewer than 20 employees, Medicare pays first and the employer plan pays second. If you skip Medicare in this situation, you can be left with claims that neither one pays — plus lifetime late-enrollment penalties.
What this means for you
- You generally need to enroll in Medicare Parts A and B even while the employer coverage continues.
- The employer plan may still add value as secondary coverage — that's worth reviewing before you drop anything.
- The first real decision after enrolling is Supplement vs. Advantage — and that conversation should come before any plan names.
Prefer to talk it through? Call me directly: (352) 464-4400
This is an initial, educational read based on your answers — not enrollment advice. Your exact situation (plan documents, employer notices, and timing) should be verified before making a change.
Enrolling in Medicare looks like the right move — and the clock may be running.
Here's what surprises most people: COBRA and retiree coverage don't count as active employer coverage in Medicare's eyes. Your window to enroll in Part B without penalty runs for 8 months from when active employment ended — no matter how long the COBRA or retiree plan lasts.
What this means for you
- Missing the 8-month window can mean a permanent Part B penalty and waiting months for coverage to start.
- COBRA typically ends automatically once you're eligible for Medicare — another surprise that catches people mid-treatment.
- Once you're enrolled, the real decision is Supplement vs. Advantage — that's where I always start.
If your window is closing, don't wait on email — call me: (352) 464-4400
This is an initial, educational read based on your answers — not enrollment advice. Your exact dates and notices should be verified before making a change.
Based on your answers, Medicare looks like the stronger fit.
Between what you're paying, what the employer plan makes you cover out of pocket, and your healthcare needs, the math tends to favor Medicare — often with better predictability and wider doctor access, depending on the path you choose.
Why Medicare came out ahead for you
The next decision — and the one I always start with — is Supplement vs. Advantage. They work completely differently, and choosing the wrong structure is much harder to undo than people realize.
Learn What My Options AreOr call me directly: (352) 464-4400
This is an initial, educational read based on your answers — not enrollment advice. Exact premiums, plan documents, and timing should be verified before making a change.
Keeping your employer coverage likely makes sense for now.
Based on your answers, the employer plan is doing real work for you — and because the coverage is tied to active employment at a larger employer, you can delay Medicare without penalty and enroll later with a special enrollment period.
Why the employer plan came out ahead for you
The critical part is the exit plan: the moment employment ends, an 8-month clock starts — and the first 6 months of Medicare come with a one-time guarantee that never repeats. Getting the sequence right matters more than most people are told.
Get My Free Medicare ReviewOr call me directly: (352) 464-4400
This is an initial, educational read based on your answers — not enrollment advice. Confirm your plan is creditable and your timing before delaying any part of Medicare.
Yours is a genuinely close call — the details will decide it.
Some situations point clearly one way. Yours doesn't — the costs, coverage, and rules are balanced enough that the right answer comes down to specifics a quiz can't see: the plan's actual benefit summary, your medications, your doctors, and your timeline.
The factors pulling in each direction
This is exactly the kind of situation I built my practice around — a side-by-side comparison of your real numbers, with no pressure toward either answer. I'm paid by carriers when someone enrolls, so the review itself costs you nothing.
Schedule My Free Medicare ConsultationOr call me directly: (352) 464-4400
This is an initial, educational read based on your answers — not enrollment advice.