Working past 65, then retiring
Many people in Edmond and Oklahoma City keep a job's group health plan past 65 and delay Part B. When that job or coverage ends, Medicare gives you a Special Enrollment Period. You can sign up for Part B any time while you still have group coverage based on current employment, or during the 8 months after the employment or the coverage ends, whichever happens first. If you use this window, you generally avoid the Part B late enrollment penalty.
COBRA and retiree coverage are not coverage based on current employment, so they don't extend that 8-month window. Plan your Part B start date before the clock runs out. If you sign up for Part B while still working, or within the first full month after employer coverage ends, Medicare.gov says you can ask to delay your Part B start date up to 3 months. If your job-based drug coverage is creditable, also line up Part D so you don't go 63 days or more without creditable drug coverage, which can trigger a lifelong Part D penalty.
Your Medigap Open Enrollment Period starts with Part B
If you delayed Part B, your six-month Medigap Open Enrollment Period starts the first month you're both 65 or older and enrolled in Part B. During it, you can buy any Medicare Supplement sold in Oklahoma without health questions. For many retirees this is the best time to get a Plan G or Plan N.
Guaranteed-issue rights if employer coverage ends
If you already have Medicare and your employer or union group plan that paid after Medicare is ending, federal rules give you a guaranteed-issue right to buy certain Medicare Supplement plans. The company can't deny you or charge more because of your health. You generally have up to 63 days after the coverage ends to use this right, so keep the letter or notice showing your coverage end date.
What to do next
- Confirm the exact date your employer coverage ends.
- Sign up for Part B through Social Security so it starts when you need it.
- Compare Medicare Supplement plans and add Part D drug coverage, or review Medicare Advantage if a supplement premium doesn't fit your budget.
I'll help you line up the dates so there's no gap. Use the form above or call 405-823-2831.
Sources (checked Oct 30, 2026): Medicare.gov: When does Medicare coverage start? · Medicare.gov: When can I buy a Medigap policy? · Medicare.gov: Avoid late enrollment penalties
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Questions
Frequently asked questions
When can I sign up for Part B after I retire?
While you still have group coverage from current employment, or during the 8 months after the employment or coverage ends, whichever comes first.
Does COBRA count as employer coverage for Medicare?
No. COBRA is not coverage based on current employment, so it doesn't extend your Part B Special Enrollment Period.
Can I get a Medicare Supplement without health questions after retiring?
Usually, yes, during your six-month Medigap Open Enrollment Period, which starts when you're 65 or older and enrolled in Part B. Certain guaranteed-issue situations, like losing employer coverage that paid after Medicare, also apply.
Does it cost anything to work with you?
No. You don't pay me anything to work with me. Licensed agents are paid by the insurance company.
Talk with a local licensed agent
No cost to work with me. No pressure to enroll.
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