Your Situation
Losing Your Coverage — Your Deadlines and Your Rights
When health coverage ends without your choosing, the clock starts right away. The good news: losing coverage usually opens a special window to get new coverage — and sometimes gives you rights you wouldn't otherwise have. The key is acting before those windows close.
Find Your Situation
I'm 65+, losing work coverage, and haven't signed up for Part B
This includes a layoff, retiring, or your employer dropping its health plan. You have an 8-month Special Enrollment Period to sign up for Part B with no penalty, starting when your job or your work coverage ends — whichever comes first. You have 63 days to get drug coverage.
I'm on COBRA
COBRA doesn't count as current work coverage. Your 8-month Part B window started when your job ended, not when COBRA ends. If you're already eligible for Medicare, don't wait for COBRA to run out — sign up for Part B now. Also ask your plan: COBRA can end early once you become entitled to Medicare.
My retiree plan or employer plan that works with Medicare is ending
If you already have Parts A and B and your employer or union coverage that pays after Medicare is ending, you have a guaranteed right to buy a Medicare Supplement. You can also join a Medicare Advantage or drug plan during a Special Enrollment Period.
My Medicare Advantage plan is leaving my area or not renewing
You'll get a notice from the plan, usually in the fall. You can choose a different Medicare Advantage plan, or go back to Original Medicare and buy a Medicare Supplement with guaranteed issue rights. If you do nothing, you'll be moved to Original Medicare, and you'll need to pick a drug plan.
I'm losing Medicaid
You get a Special Enrollment Period to change your Medicare Advantage or drug plan. If you had Extra Help through Medicaid, it usually continues through the end of the year. Check whether you still qualify for a Medicare Savings Program.
My spouse is losing work coverage that covered me
The same rules apply to you as if the coverage were your own — the 8-month Part B window and 63-day drug coverage deadline start when your spouse's job or the coverage ends.
The Deadlines That Matter
| What | Deadline | If you miss it |
|---|---|---|
| Sign up for Part B | 8 months after work or work coverage ends | Wait for General Enrollment (Jan–Mar) and possibly a lifelong penalty |
| Get Part D or a plan with drug coverage | 63 days without creditable drug coverage | A Part D penalty added to your premium for as long as you have Medicare drug coverage |
| Medicare Supplement guaranteed issue | Generally 63 days after your coverage ends | Insurers can review your health and may charge more or decline you |
Keep your paperwork. Save the letter or notice that says your coverage is ending, plus any proof of the dates you were covered. You may need it to prove you qualify for a Special Enrollment Period or a guaranteed issue right.
Why Guaranteed Issue Rights Matter in Wisconsin
Outside of your first 6 months on Part B, Wisconsin Medicare Supplement insurers can usually ask health questions and turn you down. Losing certain kinds of coverage is one of the few times you get a second chance with no health questions asked.
If you've been on Medicare Advantage and would rather have a Supplement, losing your plan may be your best opportunity to switch. Don't let the window close before you've compared both paths.
How Wisconsin Medicare Supplements are different → | Medicare Advantage vs. Supplement →
Under 65 in the Household?
Medicare only covers the person who's eligible. If a spouse or dependent under 65 was on the same work plan, losing that coverage gives them a 60-day Special Enrollment Period to get a Marketplace (ACA) plan. They may qualify for savings based on household income. We help Wisconsin families with both Medicare and Marketplace coverage.
Retiring From Work
Step-by-step transition guide →
Missed Your Window?
Late penalties and how to fix them →
Still have questions? Talk with Marit.
Licensed Wisconsin agent in downtown Appleton. No cost to talk, no pressure to enroll.
Or send us a message →