Your Situation
Retiring From Work — Your Medicare Transition Guide
If you delayed Medicare because you had employer coverage, you're now in a time-sensitive transition. Done right, this is smooth. Done wrong, you could face permanent premium penalties or a gap in coverage.
You Have a Special Enrollment Period
When you leave employer coverage, you qualify for a Special Enrollment Period (SEP) — an 8-month window to enroll in Medicare Part B without paying the late enrollment penalty.
The 8-month SEP starts when your employer coverage ends — not when you retire.
The SEP only applies if you were covered by an employer group health plan through your own or a spouse's current employment.
COBRA does not count as "current employer coverage." Once you're on COBRA, your SEP clock has already started.
Marketplace (ACA) plans also do not count as creditable coverage for the Part B SEP — enroll in Medicare first.
Important: Don't wait until the last minute. Enroll in Part B as soon as your employer coverage ends, or even before if you know the end date. The 8 months sounds like a lot — but plan selection and processing take time.
What to Do and In What Order
Confirm your Part A enrollment
Most people get Part A for free at 65. If you were auto-enrolled, you're all set. If you deferred, sign up now — Part A covers inpatient hospital care.
Enroll in Part B
Contact Social Security (ssa.gov or 1-800-772-1213) and provide proof that you had employer coverage. They'll assign your Part B effective date.
Choose your coverage path
Once you have Part A and B, decide between Medicare Advantage (MAPD) or Original Medicare with a Supplement (Medigap). At this transition, Wisconsin gives you guaranteed issue rights for Medigap — you can't be denied for health reasons.
Add Part D if needed
If you choose Original Medicare, add a standalone Part D drug plan within 63 days of your employer drug coverage ending to avoid a late enrollment penalty.
Cancel COBRA or retiree coverage (if applicable)
Once your Medicare coverage is active, you generally won't need COBRA. Some retiree plans from employers coordinate with Medicare — check with your HR department before canceling.
Choosing Your Coverage Path
This is the biggest decision you'll make at retirement. Medicare Advantage (MAPD) and Medicare Supplement (Medigap) both cover your healthcare — but they work very differently.
⭐ Medicare Advantage
Lower monthly premiums, all-in-one plan with drug and often dental/vision. You use the plan's network and pay copays when you receive care.
🛡️ Medicare Supplement
Higher monthly premiums, but maximum flexibility — see any doctor or specialist in the US who accepts Medicare. Very predictable out-of-pocket costs.
Full side-by-side comparison → | Estimate your monthly Medicare costs →
Part D and Your Prescriptions
Your employer drug coverage likely had a different formulary than any Medicare Part D plan. When you transition to Medicare, check that your current medications are covered — and at what cost tier — under the plan you're considering. Drug costs can vary significantly between plans, even for the same medication.
Part B – Medical
Enrollment, costs, and late penalties →
MAPD vs. Medicare Supplement
Full side-by-side comparison →
My Medicare Budget
Estimate your monthly costs →
Questions about your retirement Medicare transition?
We help Wisconsin residents navigate this transition every day — at no cost. We'll compare plans across all available carriers in your county.
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