
Of course, turning 65 doesn’t mean you have to retire—but it does mean Medicare eligibility begins, and many people still wonder:
“If I’m still working and have health insurance through my employer, do I need to enroll in Medicare when I turn 65?”
The answer depends on several factors—including your employer size, your current health coverage, and whether you’ve already started Social Security. At Emerald Medicare, we help clients evaluate these decisions every day to avoid penalties, gaps, or unnecessary costs.
Let’s break it down…
✅ Start with Medicare Part A: Most People Enroll
Medicare Part A (hospital insurance) is premium-free for most people and generally covers inpatient hospital stays, skilled nursing, and hospice care.
- If your employer has coverage and you’re still working, you can usually enroll in Part A at 65 without any downside.
- HOWEVER—if you’re contributing to a Health Savings Account (HSA), you may want to delay Part A to avoid tax issues.
🧾 What About Part B? It Depends on Employer Size
Medicare Part B covers outpatient care, doctor visits, and preventive services. Unlike Part A, you do pay a monthly premium for Part B—so enrolling unnecessarily could cost you.
IF YOUR EMPLOYER HAS 20 OR MORE EMPLOYEES:
- You can delay enrolling in Part B without penalty.
- Your employer coverage remains primary, and Medicare is secondary.
- You’ll qualify for a Special Enrollment Period (SEP) when you retire or lose coverage—no late penalty.
IF YOUR EMPLOYER HAS FEWER THAN 20 EMPLOYEES:
- You must enroll in Medicare Part A and B when first eligible.
- In this case, Medicare becomes your primary insurance, and your employer plan pays second—or not at all.
- Failing to enroll could leave you uninsured and/or penalized.
Always check with your HR department—don’t assume your employer coverage counts as “creditable” for Medicare.
💼 Still Working with an HSA? Be Careful
If you’re contributing to a Health Savings Account (HSA) and you enroll in any part of Medicare, including Part A, you must stop HSA contributions.
- Enrollment in Medicare (even Part A) disqualifies you from contributing.
- Retroactive Part A enrollment (up to 6 months) can create IRS penalties if you’re not careful.
- We typically recommend stopping HSA contributions at least 6 months before you apply for Medicare.
📍 Why It Matters
Making the wrong choice about when to enroll can lead to:
- Late enrollment penalties
- Gaps in coverage
- Unexpected bills if Medicare should have paid primary
- Tax consequences for HSA users
✅ When to Enroll (or Delay) Original Medicare: A Quick Recap
Situation | Part A | Part B |
Employer has 20+ employees, no HSA | Usually enroll | Delay OK |
Employer has fewer than 20 employees | Enroll | Enroll |
Still working and using an HSA | Delay | Delay |
Retiring soon or leaving coverage | Enroll | Enroll (within 8 months of losing coverage) |
Click below to schedule an appointment with one of our Medicare Experts.
Or, Contact Us
📞 (888) 683-6372 or (845) 358-1220
📧 office@emeraldmedicare.com
back to blog