Dear wise senior,
My wife and I are nearing 65, still employed, and have solid health insurance through our jobs. Should I be enrolling in Medicare now?
–Almost 65 years old
Dear Almost
If either of you continues to work past 65 with employer-provided health insurance, delaying Medicare enrollment could be an option without incurring a late penalty. That said, the specifics can differ based on your employer’s size.
Here’s a quick recap: Original Medicare has two parts. Part A is for hospital coverage and is typically free. Part B covers doctor visits, tests, and outpatient services, costing $202.90 monthly in 2026. Higher income earners, those making over $109,000 individually or $218,000 as a couple, will face higher premiums.
If you’re still working
To figure out how your employer’s insurance integrates with Medicare, your first step should be to speak with HR or your benefits manager. Generally, enrolling in Part A is a good idea since it’s free, though keep in mind that if you’re putting money into a Health Savings Account, enrolling in Part A could interrupt those contributions.
Whether you need to sign up for Part B largely depends on your employer’s size.
Small employer
If your workplace has fewer than 20 employees, Medicare becomes your primary coverage. In this case, you must enroll in Part B during your initial enrollment period, which spans seven months: three months before your 65th birthday, the month of your birthday, and three months after.
If you’re not yet receiving Social Security, you’ll need to apply for Medicare yourself. This can be done online, by calling 1-800-772-1213, or visiting your local Social Security office directly.
If you miss the initial enrollment window, you’ll need to wait for the general enrollment period, which runs from January 1 to March 31 each year. Coverage starts the month after you enroll, but you could face a 10% penalty on your Part B premium for each year you waited. Signing up on time is crucial to bypass any gaps in coverage and additional expenses.
Large employer
If there are 20 or more employees at your workplace, group health insurance will serve as your primary coverage as long as you’re actively employed. In this scenario, if your coverage is robust enough, enrolling in Part B when you turn 65 isn’t necessary. If you do enroll, Medicare will be your secondary insurance.
When your job or employer coverage ends, you’ll have a special eight-month enrollment window to register for Part B without facing penalties.
Check drug coverage
It’s also wise to review your prescription drug coverage. Check with your benefits representative to determine if your employer’s plan qualifies as “creditable.” If it does, enrolling in a Medicare Part D plan is unnecessary. If not, you should sign up for Part D during your initial enrollment to avoid penalties, which generally amount to 1% of the national average premium for each month you’re late.
You can compare Part D plans at: medicare.gov/plan-compare.
Need help?
For complimentary guidance, reach out to the State Health Insurance Assistance Program at 1-877-839-2675 or visit shiphelp.org. You can also contact the Medicare Rights Center Helpline at 1-800-333-4114.
Navigating Medicare while still working can be a bit tricky, but discussing with your employer and grasping the rules can help you avoid expensive errors. Taking the time to enroll now will ensure you have the coverage you need without unnecessary penalties later on.
