How do I switch from employer coverage to Medicare without a penalty in 2026?

How do I switch from employer coverage to Medicare without a penalty in 2026?
If you’re leaving employer coverage, you get an 8-month Special Enrollment Period for Part B and 63 days for Part D. Enroll before your group plan ends and coverage starts the first of the following month. Miss the window and you face a lifetime Part B penalty of 10% for every 12 months you delayed.
Leaving employer coverage? Get a Medicare review before you enroll.
We compare your group plan against Medicare, protect your guaranteed-issue rights, and file the paperwork so there’s no gap and no penalty.
Founder, The Modern Medicare Agency · 18+ years of Medicare experience Licensed independent broker · Content reviewed for accuracy in 2026
Not sure which Medicare option is right for you?
Get a free Medicare review before you choose a plan. We’ll help you compare costs, doctors, prescriptions, and enrollment timing — with no pressure and no cost.
Employer Coverage vs. Medicare: What Changes
Feature Employer Group Plan Medicare + Supplement + Part D
Monthly cost to you Employee share of premium $185 Part B + $110–$170 Medigap + Part D
Spouse/dependent coverage Usually included Each person enrolls separately
Deductible $1,500–$5,000 typical $257 Part B deductible (Plan G)
Network Deductible Any US doctor accepting Medicare
Drug coverage Bundled Separate Part D plan
Enrollment window Open enrollment once a year 8-month SEP after coverage ends
Common mistakes to avoid
It does not for Part B. People on COBRA past 65 routinely trigger a permanent Part B penalty and a coverage gap of several months.
Form CMS-L564 has to be signed by your employer. Start 60–90 days out so Part B begins the day your group plan ends.
Form CMS-L564 has to be signed by your employer. Start 60–90 days out so Part B begins the day your group plan ends.
Part B gives you 8 months. Part D only gives you 63 days — and the drug penalty is charged for life.
Talk to an advisor 3–6 months before your employer coverage ends, or as soon as you know your retirement date. We compare your employer plan’s true cost against Medicare, coordinate spouse coverage, and file the enrollment forms so there is no gap and no penalty.
The most expensive Medicare mistake I see isn’t picking the wrong plan — it’s timing. A retiring executive stayed on COBRA for nine months thinking he was covered. He paid a Part B penalty every month for the rest of his life. Ten minutes on the phone would have prevented it.
“Paul made Medicare feel simple. He walked us through the trade-offs, ran the numbers for our prescriptions, and never once pushed us into a plan. We saved over $1,800 in the first year.”
Not sure which Medicare option is right for you?
Get a free Medicare review before you choose a plan. We’ll help you compare costs, doctors, prescriptions, and enrollment timing — with no pressure and no cost.

If your employer has 20+ employees, you can usually delay Part B without penalty while you have active group coverage. If your employer has fewer than 20 employees, Medicare typically becomes primary at 65 and you should enroll.

You have an 8-month Special Enrollment Period for Part B starting the month after employment or group coverage ends — whichever comes first — and 63 days for Part D.

Not for Part B. COBRA can count as creditable drug coverage in some cases, but it does not protect you from the Part B late-enrollment penalty.

Yes, through an ICHRA or retiree HRA. Employers with 20+ employees cannot pay Medicare premiums directly for active employees, but retiree arrangements are permitted. Bring your plan documents to your review.


If your spouse is under 65 they’ll need marketplace or their own employer coverage. We map both people’s timelines together so nobody ends up uninsured.

Often yes, once you compare total cost — premium plus deductible plus out-of-pocket max. Bring your employer plan’s summary of benefits and we’ll run the side-by-side.

In most states, losing employer group coverage triggers a guaranteed-issue window — typically 63 days — where carriers must sell you certain Medigap plans with no health questions.

CMS-40B (Part B application) and CMS-L564 (proof of employer coverage, signed by HR). We help clients complete both.

A month-by-month checklist with every form, deadline, and question to ask HR before your group plan ends.

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