Shelton, Connecticut & Glastonbury, Connecticut
Mon-Fri 8:30 am - 7:00 pm, Sat 8:30-2:30 Sun: Closed
CALL TO SCHEDULE AN APPOINTMENT
Understanding Medicare eligibility is a key step in planning for retirement healthcare. Eligibility determines when you can enroll, which plans you can choose, and whether you may face penalties if you delay.
At Retire With Medicare, we help you understand not just if you qualify — but how and when to take action so you can avoid costly mistakes.
Age
Disability status
Certain medical conditions
Work history or a spouse’s work history
You are a U.S. citizen or legal resident
You or your spouse worked and paid Medicare taxes for at least 10 years (40 quarters)
You are eligible for Medicare Part A and Part B
You can choose Original Medicare or Medicare Advantage
You may add Part D or Medigap coverage
You have received Social Security Disability Insurance (SSDI) for 24 consecutive months
You are automatically enrolled in Medicare Part A and Part B in most cases
You can choose Medicare Advantage or add prescription drug coverage
Permanent kidney failure requiring dialysis or a transplant
Eligibility rules and enrollment timing vary
Coverage may be temporary or ongoing depending on circumstances
Medicare eligibility begins immediately once SSDI benefits start
No waiting period applies
You or your spouse worked at least 10 years and paid Medicare taxes
If not:
You may still enroll, but a monthly premium may apply
Available to anyone who qualifies for Medicare
Requires a monthly premium
Enrollment timing is critical to avoid late penalties
Size of your employer (usually 20 or more employees)
Whether your employer coverage is considered creditable
Whether you can delay Part B enrollment without penalty
Initial Enrollment Period (IEP)
Special Enrollment Period (SEP)
General Enrollment Period (GEP)
Late enrollment penalties
Delayed coverage
Higher lifetime costs
❌ “I’m automatically enrolled at 65 no matter what.”
✔ Automatic enrollment depends on Social Security benefits.
❌ “I don’t need Medicare if I’m still working.”
✔ This depends on your employer size and coverage type.
❌ “Eligibility means coverage starts automatically.”
✔ You must still enroll to activate coverage.
Enroll on time
Avoid penalties
Choose the right coverage
Protect your retirement savings
Not sure when or how you qualify for Medicare? We’re here to help.
Confirm your Medicare eligibility
Understand how work or disability affects enrollment
Get guidance tailored to your situation
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Shelton, Connecticut / Glastonbury, Connecticut
Mon-Fri 8:30 am - 7:00 pm, Sat: 8:30 - 12:30 Sun: Closed
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