Do I Need Medicare If I’m Still Working at 65? What to Know in Virginia
Melody Key | Mar 30 2026 17:00
One of the most common questions people ask when approaching retirement age is:
“Do I need Medicare if I’m still working at 65?”
The answer depends on your specific situation—especially the type of health insurance you currently have. For many individuals in Bedford, Lynchburg, Roanoke, and surrounding Virginia communities, making the wrong decision at this stage can lead to unnecessary costs or long-term penalties.
Understanding how Medicare works alongside employer coverage can help you make the right choice.
Why This Decision Matters
Turning 65 does not automatically mean you need to enroll in every part of Medicare right away. However, delaying enrollment without the right type of coverage can result in lifetime penalties, particularly for Medicare Part B and Part D.
This is why reviewing your coverage before making a decision is important.
When You May Not Need Medicare Right Away
If you are still working and covered under an employer health plan, you may be able to delay Medicare Part B without penalty.
This typically applies if:
- You are actively employed (not retired)
- Your coverage comes from your current employer or your spouse’s employer
In these cases, your employer insurance may remain your primary coverage, and Medicare can be delayed until that coverage ends.
The Key Factor: Employer Size
One detail many people overlook is the size of the employer providing the coverage.
If the employer has 20 or more employees, your employer plan is usually considered primary, and Medicare can often be delayed.
If the employer has fewer than 20 employees, Medicare may become your primary coverage at age 65. In this situation, delaying Medicare could leave you with gaps in coverage.
Because of this, it’s important to confirm how your plan is classified before making any decisions.
Coverage That Does NOT Allow You to Delay Medicare
Not all insurance counts as “creditable” coverage for delaying Medicare. Many people assume they are covered when they are not.
Coverage that typically does not qualify includes:
- COBRA
- Retiree health plans
- Marketplace (ACA) plans
- VA coverage on its own
If you rely on one of these, you generally should enroll in Medicare when you first become eligible.
What Happens If You Delay Incorrectly
If you delay Medicare without having qualifying coverage, you may face late enrollment penalties.
For Part B, this penalty is added to your monthly premium and continues for as long as you have Medicare. For Part D, a similar penalty applies if you go without creditable prescription coverage.
These penalties are not one-time fees—they are ongoing and can increase your costs over time.
What If You Plan to Keep Working?
Many individuals choose to continue working past 65, either full-time or part-time. In these cases, Medicare decisions should be coordinated with your employer coverage.
Some people enroll in Part A only and delay Part B. Others enroll in both, depending on how their employer plan works.
There is no one-size-fits-all answer, which is why reviewing your situation in advance is important.
Health Savings Accounts (HSA) Considerations
If you contribute to a Health Savings Account, Medicare timing becomes even more important.
Once Medicare begins, you are no longer allowed to contribute to an HSA. Because Medicare Part A can be applied retroactively, contributions must stop ahead of time to avoid tax penalties.
This is a detail many people miss, and it can create unexpected issues if not handled properly.
Transitioning to Medicare Later
If you delay Medicare due to employer coverage, you will typically qualify for a Special Enrollment Period when that coverage ends.
This allows you to enroll in Medicare without penalty, as long as you act within the required timeframe.
Missing this window can result in delays and additional costs, so timing remains important even when delaying is allowed.
Common Mistakes to Avoid
Many people assume they can simply “sign up later” without consequences. Others believe all coverage qualifies for delaying Medicare.
In reality, the most common mistakes include:
- Not verifying whether employer coverage qualifies
- Assuming COBRA or retiree coverage counts
- Missing the Special Enrollment Period after leaving a job
- Not reviewing how Medicare works with current benefits
These issues can usually be avoided with a quick review before making a decision.
Why Local Guidance Makes a Difference
When searching for answers, many people turn to general information online. While helpful, it often doesn’t reflect the specifics of your employer plan or local coverage options.
Working with a local Medicare agent in Bedford, VA allows you to review your situation based on real-world factors, including your employer coverage, providers, and available plans in your area.
It also gives you a reliable point of contact when your situation changes.
Making the Right Decision for Your Situation
The decision to enroll in Medicare while still working comes down to a few key factors: your current coverage, your employment status, and your future plans.
Taking the time to review these details now can help you avoid penalties, maintain continuous coverage, and make a smoother transition when the time comes.
Talk with a Medicare Agent in Bedford, VA
If you are turning 65 and still working, it’s worth reviewing your situation before making any decisions.
Croft Insurance Services, Inc. helps individuals throughout Bedford, Lynchburg, Roanoke, and surrounding Virginia communities understand how Medicare works with employer coverage and when to enroll.
Call 540-586-3500 or submit a request through the contact form to speak with a local agent.

