Medicare and Retirement
Planning to retire soon? Let’s make sure Medicare fits into your next chapter.
Whether you’re getting ready to retire or just exploring your options, understanding how Medicare fits with your employer coverage is key to avoiding gaps in care or costly penalties
Let’s break it down together.
“I’m Retiring — When Should I Sign Up for Medicare?”
If you’re leaving your job or your employer coverage is ending, you have an 8-month Special Enrollment Period to sign up for Medicare — but don’t wait.
You should contact Social Security before your employer coverage ends to avoid any lapse in coverage.
How Do I Enroll in Medicare After Leaving Employer Insurance?
You can enroll in Medicare:
Once your paperwork is submitted, you’ll typically receive your Medicare card within 3–4 weeks.
Important: COBRA and retiree health coverage do not count as creditable coverage. That means if you delay signing up for Medicare, you could face permanent late enrollment penalties. Don’t wait — enroll when you’re first eligible.
Still Working at 65? Here’s What You Need to Know
If you (or your spouse) are still working and have employer health coverage when you turn 65:
- Contact your HR or benefits administrator to understand how your coverage works with Medicare
- If your employer has 20 or more employees, you may be able to delay enrolling in Part B without penalty
- Once you leave your job or lose employer coverage, you’ll have 8 months to enroll in Part B penalty-free
Pro Tip: Keep a letter from your employer confirming when your group coverage ends. You may need it to qualify for a Special Enrollment Period or Medigap without medical underwriting.
Employer Coverage vs. Retiree Coverage — Know the Difference
There’s a big difference between being actively covered by an employer and being covered under retiree health benefits.
If you’re turning 65 and still working:
- You may delay Part B (and its monthly premium) if your employer has 20+ employees
- If your employer has fewer than 20 employees, you’ll likely need to enroll in Medicare Part B even if you’re still working
Tip: Even if you don’t take medications now, it’s usually a good idea to enroll when you’re first eligible to avoid late enrollment penalties down the road.
If you’re retiring, here’s what to consider about retiree coverage:
Can You Keep Your Employer Coverage?
- Employers aren’t required to offer retiree coverage, and even if they do, they can change or cancel it at any time
- Some retiree plans only offer "stop-loss" coverage, which kicks in only after you’ve reached high out-of-pocket limits
What Happens When You Become Eligible for Medicare?
- Some retiree plans won’t pay anything if you were eligible for Medicare but didn’t enroll
- To keep full benefits under most retiree plans, you must enroll in both Part A and Part B
How Will Your Retiree Coverage Work With Medicare?
- Ask your employer for a Summary Plan Description or benefit booklet
- Or talk to your benefits administrator to understand how coverage coordinates with Medicare
Let’s Make Your Transition Smooth
At Tailored Medicare, we help you:
- Know exactly when and how to enroll in Medicare
- Understand your employer or retiree coverage
- Avoid penalties and coverage gaps
- Get support for your spouse or dependents if needed
Retiring soon?
to talk through your situation and create a step-by-step plan. We’ll make sure Medicare works for you — not the other way around.