How to Get Medicare While Working?
How to Get Medicare While Working — More Americans than ever are working past age 65, and with that comes one of the most common questions we hear: “Do I need to sign up for Medicare if I’m still covered by my employer?” The answer depends on your situation. At Diversified Insurance Brokers, our goal is to help you make this transition confidently — ensuring you avoid unnecessary premiums, penalties, and gaps in coverage.
Medicare eligibility begins at 65, but that doesn’t mean you must enroll right away. Whether you should sign up immediately or wait depends on your employer’s health plan, company size, and how long you plan to continue working. Making the right decision can save you thousands in the long run.
How Medicare and Employer Coverage Work Together
When you’re covered through work, Medicare often works as a secondary payer, but not always. The key factor is employer size. If your company has 20 or more employees, your group plan remains primary, and Medicare becomes secondary. If your company has fewer than 20 employees, Medicare becomes your primary insurance once you turn 65. That distinction determines whether you need to sign up for Parts A and B now or later. Learn more in our guide on Medicare Supplement vs Medicare Advantage.
When Should You Enroll?
Most people enroll in Medicare Part A when they turn 65 because it’s premium-free if you’ve worked and paid Medicare taxes for at least 10 years. However, if you contribute to an HSA (Health Savings Account), you’ll need to delay enrollment in Part A to continue making contributions. Our HSA and retroactive Part A guide explains how to time your decision properly to avoid IRS penalties.
If you delay enrolling in Parts B or D while working, you’ll need to make sure your employer coverage is “creditable” — meaning it’s as good or better than Medicare’s. When you retire, you’ll qualify for a Special Enrollment Period (SEP) to join without penalties. Timing this correctly ensures a smooth handoff from your employer plan to Medicare.
Common Mistakes to Avoid
We often see people unintentionally trigger penalties or lose access to their HSA funds. Enrolling in Part A even one day before receiving Social Security benefits will stop your ability to contribute to an HSA. Additionally, waiting too long to enroll in Part B after leaving employer coverage can result in lifelong premium penalties. These are completely avoidable with proper planning.
Another frequent oversight involves comparing Medicare Advantage to traditional Medicare. Some assume they’re the same, but Advantage plans bundle hospital, medical, and sometimes prescription coverage into one. For those leaving employer coverage, comparing Medicare Advantage vs Medicare Supplement options is key to finding the right fit.
Example: Transitioning the Right Way
Consider Michelle, age 66, who works for a company with 35 employees. At 65, she enrolled in Medicare Part A but delayed Part B because her employer coverage was strong. Two years later, when she retired, she used her SEP to enroll in Part B and a supplement plan. Because she acted on time, Michelle avoided late penalties and had no lapse in coverage — all while saving money by comparing low-cost Medicare plans for retirees.
Estimate Your Medicare Costs
Use our free calculator to estimate your Medicare costs and compare how it fits with your current employer plan. You can review premiums, deductibles, and supplement options side-by-side.
Preparing for Retirement and Enrollment
As you approach retirement, it’s smart to begin reviewing your Medicare options 2–3 months before your last day of work. That window gives you time to apply for Part B, choose your supplement or Advantage plan, and ensure drug coverage aligns with your prescriptions. Many clients also explore Medicare plans with dental and vision coverage for complete protection.
Need Guidance? Talk with Tonia
If you’re unsure about timing or how your current employer plan compares to Medicare, Tonia Pettitt — our Medicare specialist at Diversified Insurance Brokers — can help review your situation and provide clear, personalized guidance.
Let’s Avoid Costly Medicare Mistakes Together
Book a free consultation with Tonia to ensure your Medicare enrollment is complete, correct, and optimized for your needs.
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FAQs: How to Get Medicare While Working
Do I have to enroll in Medicare at 65 if I’m still covered by my employer?
No. If your employer coverage is creditable, you can delay Parts B and D until retirement without penalty.
Should I enroll in Medicare Part A while working?
Usually yes, because it’s premium-free. But if you contribute to an HSA, delay enrollment until after your final contribution.
What happens when I retire or lose employer coverage?
You’ll have an 8-month Special Enrollment Period to sign up for Part B and 63 days for Part D without penalties.
What is “creditable coverage” for Medicare?
It means your employer plan’s benefits are as good or better than Medicare’s. Your HR department can confirm this in writing.
Can I stay on my employer plan and also have Medicare?
Yes. For large employers (20+), your group plan stays primary, and Medicare becomes secondary coverage.
What if my company has fewer than 20 employees?
In that case, Medicare usually becomes your primary insurance once you turn 65, so enrolling in Parts A and B is essential.
Can I keep contributing to an HSA after joining Medicare?
No. Once you enroll in any part of Medicare, you can no longer make HSA contributions. You can still use your funds for qualified expenses.
Will I pay penalties for delaying Medicare?
Only if you go without creditable coverage. Always verify with your employer before choosing to delay enrollment.
Can my spouse enroll in Medicare if I’m still working?
Yes, your spouse can enroll once they turn 65, even if they remain on your employer plan.
Who can help me understand my timing and options?
Tonia Pettitt, our licensed Medicare specialist, offers free consultations to help ensure you enroll correctly and avoid penalties.
