If you’re 65 or older and still working—or your spouse is—you can absolutely have both Medicare and employer-based health insurance. In fact, combining them can often be a smart move.
What’s Inside
- Employer Size Matters
- Coverage Coordination
- Enrollment Timing & Penalties
- Employer Drug & Health Savings Account (HSA) Considerations
- Retiree Coverage & COBRA
- In a Nutshell
Employer Size Matters
- Large employers (20+ employees): Your employer plan pays first, and Medicare covers what’s left. This means you can delay Medicare Part B enrollment without penalty while you’re working.
- Small employers (<20 employees): Medicare becomes the primary payer, so you’ll generally need to enroll in both Part A and Part B to avoid coverage gaps or denial of claims.
Coverage Coordination
In Medicare terms, the total bill is shared between:
- Primary payer (who pays first, up to its coverage limits)
- Secondary payer (who covers remaining costs, if any)
Large‑employer insurance usually covers first, with Medicare topping off. Small employers flip that order.
Enrollment Timing & Penalties
Your Initial Enrollment Period (IEP) begins 3 months before your 65th birthday and ends 3 months after.
- Large employer plans: Delay Part B enrollment until work ends—no penalties. But enroll in Part A (usually premium‑free) during your IEP.
- Small employer plans: You must sign up for both Parts A & B during your IEP to avoid late penalties.
If you miss the IEP, you may qualify for a Special Enrollment Period (SEP) lasting up to 8 months after leaving job-based coverage. Enrollment during SEP avoids penalties.
Employer Drug & Health Savings Account (HSA) Considerations
- Employer drug coverage: If it’s at least as good as Medicare Part D—called creditable coverage—you can delay Part D enrollment without penalty medicare.gov+15go.cms.gov+15ehealthinsurance.com+15.
- HSAs: If you contribute to an HSA, you must stop contributions 6 months before activating Medicare to avoid tax consequences.
Retiree Coverage & COBRA
- Retiree insurance typically behaves like large-employer insurance—Medicare pays second and you’ll still need both Parts A & B.
- COBRA after leaving work: Medicare becomes primary—unless you have ESRD, in which case COBRA remains primary for the first 30 months.
| Question | Why It Matters |
| Who pays first? | Company size determines if Medicare or your employer health plan is primary |
| Do you have creditable drug coverage? | Avoid Part D penalties by delaying if your plan qualifies |
| Are you contributing to an HSA? | Stop 6 months before Medicare to avoid taxes |
| When does employer coverage end? | Acts as a SEP trigger for Medicare enrollment |
| Do you plan to retire soon? | Part A is often premium-free, so enrolling early may offer extra coverage at no cost |
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In a Nutshell
Yes—you can have both Medicare and employer insurance.
✔️ If you’re with a large employer: enroll in Part A at 65, delay Part B while working, then enroll during your SEP when coverage ends.
✔️ If you work for a small employer: enroll in both Parts A & B during your IEP.
Avoid Medicare penalties by understanding your employer’s size, coverage quality, and enrollment windows.
Have a question specific to your situation? A State Health Insurance Assistance Program (SHIP) counselor or your employer benefits officer can guide you.
📞 Need one-on-one help? Our local experts are here to guide you through every step.
👉 Visit SecureSafer.com or call (646) 444-2020
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