Medicare Help
Retiring After 65: Moving From Employer Coverage to Medicare
If you kept working past 65 and delayed Medicare, you'll have a special window to enroll when you retire. Here's how to make the switch smoothly.
In short
If you delayed Part B because you had group health coverage from your (or your spouse's) current employment, you generally have an 8-month Special Enrollment Period to sign up — starting the month after the employment or coverage ends, whichever happens first. Plan ahead so there's no gap.
Step by step
Plan 2–3 months ahead
Pick your target Medicare start date — ideally the day after your employer coverage ends.
Get your employer form signed
Ask your employer to complete Form CMS-L564 (Request for Employment Information), which shows you had group coverage.
Apply for Part B
Submit Form CMS-40B (Application for Enrollment in Medicare Part B) to Social Security, along with the employer form. You can also apply online through Social Security.
Choose your coverage
Pick a Medicare Advantage plan, or a Medigap policy plus a Part D plan. Some enrollment windows are short, so don't wait.
Watch these time limits
- To join a Medicare Advantage or Part D plan after losing employer coverage, you generally have 2 full months after the month your coverage ends.
- Your Medigap Open Enrollment Period starts when your Part B begins — a one-time 6-month window.
COBRA and retiree coverage
COBRA and retiree health plans are not considered coverage based on current employment. If you're eligible for Medicare, relying on them instead of enrolling in Part B could lead to a penalty and gaps in coverage. Check with your benefits administrator about how retiree coverage works with Medicare.
Is your employer drug coverage creditable?
Your employer should send a yearly notice saying whether its drug coverage is "creditable." Keep that notice — it can help show you don't owe a Part D late enrollment penalty.
How I can help
I'll help you map out your timeline, understand which forms you need, and compare Medicare options so your new coverage starts right when your employer coverage ends.
Common questions
My spouse is still working. Can I stay on their plan?
If your spouse's employer coverage is based on their current employment, you may be able to delay Part B. The employer's size (20+ employees) affects whether Medicare or the employer plan pays first.
Should I sign up for Part A while I'm still working?
Many people do because it's usually premium-free. But if you contribute to an HSA, enrolling in Part A ends your ability to contribute, so talk with your tax advisor first.
This page is general educational information, not personal advice. Medicare rules, costs, and plan options change and depend on your situation. For official information, visit Medicare.gov or call 1-800-MEDICARE (1-800-633-4227; TTY 1-877-486-2048).
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