When to Sign Up for Medicare If You’re Still Working Past Age 65

If you’re still working at 65, you have a decision to make: Do you stick with your employer’s health insurance or make the jump to Medicare?

The answer here depends on the size of your employer, whether you qualify for free Medicare Part A and whether you’re contributing to a health savings account (HSA).

• If your employer has 20+ employees: You can usually delay signing up for Medicare to save money on premiums. (Most people still join Part A if it’s free.)

• If your employer has <20 employees: You typically need to sign up for Medicare now to avoid penalties and coverage gaps.

• If you have a health savings account (HSA): Don’t enroll in Medicare yet. You’ll need to stop your contributions first to avoid tax penalties.

A note for married couples: If you're covered by your spouse's employer insurance, this information also applies to you when you turn 65.

If your or your spouse's employer has 20 or more employees and a group health plan, you don't have to sign up for Medicare at 65. But you may want to sign up for certain parts of Medicare.

• Part A: If you get Medicare Part A for free, it’s worth signing up now, unless you want to continue contributing to an HSA. In some cases, Medicare Part A may cover what your employer plan doesn’t.

• Part B: You will probably want to delay enrolling in Medicare Part B unless the coverage is better and cheaper than what you’re receiving through employer insurance. Everyone pays a premium for Part B, which is $202.90 per month in 2026.

• Part D: You can also delay enrolling in Medicare Part D as long as you have creditable coverage, meaning your coverage is at least as good as the benefits provided by Medicare Part D plans. Once you’re eligible for Medicare, your current drug plan should send you an annual notice letting you know whether your coverage is creditable.

There are permanent penalties if you go too long without coverage, so you’ll want to sign up for Medicare at least a month before you stop working or lose coverage.

» MORE: When does Medicare start?

If your or your spouse's employer has fewer than 20 employees, you typically must enroll in Medicare Part A and Part B at age 65.

Medicare will act as your primary insurance. “Primary” means that Medicare pays first, then the employer insurance kicks in to pay whatever might be covered under that policy but wasn't covered by Part A. Your employer insurance can refuse to pay for services if you don’t have Medicare.

If your employer participates in a multi-employer group plan, you may be able to wait to sign up for Medicare until you or your spouse stops working or loses coverage. Confirm with your benefits advisor that your employer plan will act as primary insurance after you turn 65.

You can wait to sign up for Medicare Part D if you have acceptable drug coverage through your employer or elsewhere. Just make sure to sign up as soon as you lose coverage or leave your job.

Medicare enrollees can't contribute to an HSA. If you're saving to an HSA and want to keep doing so, you must delay enrollment in Medicare. To avoid a tax penalty, you should plan to stop making HSA contributions at least six months before signing up for Medicare if you enroll after age 65. This is because your Medicare Part A coverage starts six months before your sign up date if you delay Medicare enrollment.

» MORE: HSAs and Medicare

If you reach 65 and you’ve worked a total of approximately 10 years over your career, you’re entitled to premium-free Medicare Part A, which is your hospital insurance. Medicare Part B, which pays for doctor visits and many other outpatient services, requires a monthly premium of $202.90 per month in 2026. Medicare Part D is prescription drug coverage, and the average total monthly premium is $34.50 in 2026.

When you stop working or lose your employer coverage, you’re granted a special enrollment period (SEP) to sign up for Medicare without penalty. Once the clock starts ticking, you have:

• Eight months to sign up for Medicare Part A and Part B.

• 63 days to sign up for Medicare Part D.

COBRA and retiree coverage don’t count as employer insurance. Your window to sign up starts when your job ends.

Delaying enrollment for Medicare can have permanent consequences if you make a mistake. Here’s why it’s important to get it right:

If you have health insurance from a previous employer, such as your or your spouse’s COBRA or retiree health coverage, you need to enroll in Medicare Parts A and B when you turn 65.

If you have health benefits as a military service member or veteran, such as TRICARE or CHAMPVA, you should consult with those programs to determine when to enroll in Medicare.

» MORE: How Do I Sign Up for Medicare?