Thinking about retirement?
Line up your next coverage before work coverage ends.
Start with two dates
of work
job coverage
These may be different. Confirm both with your employer.
Check employer coverageEnd dates, family & retiree benefits
- Confirm when coverage ends for you and your family.
- Ask what retiree health and drug benefits continue.
- Get written confirmation of creditable drug coverage.
- Check how other coverage could affect your benefits.
Retiring before 65? Ask about coverage until Medicare can start.
Start Medicare on timeCOBRA won’t extend Part B deadlines
If you delayed Part B with qualifying current job coverage, you generally have 8 months after work or coverage ends, whichever comes first.
That deadline does not provide 8 months of coverage. Arrange your start date before job coverage ends.
Drug coverage has different timing. A gap of 63 days or more without creditable coverage can mean a penalty.
Compare your next coverageDoctors · medicines · budget
Compare Original Medicare, Part D, and Medigap with Medicare Advantage. Include any retiree benefits.
With Original Medicare and a standard Medicare supplement, you can see any doctor or use any hospital in the United States that accepts Medicare.
Your 6-month federal Medigap enrollment window generally starts when you’re 65 or older and Part B begins.
See the two coverage choices →Helpful resourcesOfficial guides & local seminars
Let’s talk it through.
Call (501) 760-1590Find a seminar ↗Our guidance is free to you. We’re paid by plan providers.
General education. Confirm your dates and coverage before making a change. Reviewed September 9, 2026.
Social Security & HSAPlan these decisions before enrolling
Retirement benefits
You can enroll in Medicare without starting Social Security retirement payments.
HSA contributions
Medicare enrollment affects HSA contributions. Part A can be backdated up to 6 months, but not before you’re eligible. Confirm when you and your employer should stop contributions with your benefits or tax adviser before applying.
Medicare and HSA guidance ↗