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Working at 65? Understand Your Medicare Options
Key Things to Understand
✅ It’s Your Choice
📊 Compare Coverages
💰 Cost Considerations
👥 Spouse Coverage
💊 Prescription Coverage
🏥 Provider Networks
Schedule a Free Consultation with Andy Stroman
Frequently Asked Questions
No, if you have health insurance through an employer with 20 or more employees, you do NOT have to enroll in Medicare at 65. It’s completely optional. You can keep your employer coverage and delay Medicare enrollment without any penalties.
However, if your employer has fewer than 20 employees, you MUST enroll in Medicare at 65 because Medicare becomes your primary insurance. Your employer plan will only pay secondary, and some employer plans won’t pay at all without Medicare as primary.
Not if you have qualifying employer coverage (from a company with 20+ employees). When you eventually retire or lose that coverage, you’ll have an 8-month Special Enrollment Period to sign up for Medicare penalty-free.
The penalties only apply if you don’t have creditable coverage.
If you go without creditable coverage for 63 days or more, you’ll face a permanent 10% penalty on your Part B premium for every 12-month period you could have had Medicare but didn’t enroll. COBRA and retiree coverage don’t count as qualifying employer coverage, so be careful with those.
Yes, you can have both, but it’s usually not cost-effective. If you have both, your employer insurance (from a 20+ employee company) would be primary and Medicare would be secondary. This means you’re paying for two insurances when one would likely suffice.
The only part that might make sense is enrolling in Part A* (hospital insurance) if it’s free for you, which it usually is if you’ve worked 40+ quarters. Part A can provide secondary hospital coverage at no cost. But paying for Part B while keeping employer coverage rarely makes financial sense.
*You are not allowed to contribute to a Health Savings Account (HSA) once enrolled in any part of Medicare.
This is critical and often overlooked. If your spouse is on your employer plan and you switch to Medicare, they will likely lose their coverage through your employer. Medicare doesn’t cover spouses – everyone needs their own Medicare enrollment.
If your spouse is under 65, they’ll need to find alternative coverage (marketplace, their own employer, or expensive COBRA). Many couples choose to keep employer coverage until both are Medicare-eligible to avoid this gap. If your spouse is already 65+, they can enroll in their own Medicare when you do.
This can be a deciding factor. Compare three things:
Coverage: Check if your medications are on the formulary for both your employer plan and Medicare Part D plans. Use Medicare’s Plan Finder tool to see exactly what’s covered.
Costs: Compare your current copays/coinsurance with what you’d pay under Part D. Don’t forget to factor in the Part D deductible (up to $590 in 2025) and the out-of-pocket limit ($2,000 for covered drugs in 2025).
Convenience: Medicare Advantage plans include Part D, while Original Medicare requires a separate Part D plan. Your employer plan might have simpler, all-in-one coverage.
If you take expensive or specialty medications, run the numbers carefully. Sometimes employer drug coverage is superior, sometimes Medicare Part D offers better prices. The Medicare Plan Finder tool at Medicare.gov can show you exact costs for your specific medications.