The Medicare Deadline Most People Miss (And How to Avoid It)

The Deadline: Initial Enrollment Period (IEP)

Your Initial Enrollment Period is your first window to enroll in Medicare.

It’s a 7-month period:

• 3 months before the month you turn 65
• The month of your 65th birthday
• 3 months after your birthday month

Miss it—and don’t have qualifying coverage?
You could face:

• A lifetime penalty on your Part B premium
• A Part D penalty if you don’t enroll in drug coverage
• And a delay in your Medicare start date

This is the number one most missed deadline—and we see it all the time.

Who’s Most at Risk?

You’re most at risk of missing the IEP if:

• You’re retiring at 65 and don’t know when to enroll
• You’re still working and think your employer plan lets you delay
• You’re on COBRA, a retiree plan, or an ACA/marketplace plan

Here’s the catch:

COBRA, retiree coverage, and ACA plans do not count as credible coverage for delaying Medicare.

Only coverage through active employment—your own or your spouse’s—with a company that has 20 or more employees lets you delay without penalty.

What If You Miss It?

If you miss your IEP and don’t qualify for a special enrollment period, you’ll have to wait for the General Enrollment Period, which runs each year from January 1 to March 31.

Your coverage then wouldn’t start until July.

And on top of that:

• You’ll owe a 10 percent lifetime penalty for every 12-month period you delayed Part B
• You may also owe a Part D drug penalty if you didn’t have credible drug coverage

Let’s say you turn 65 in June and don’t enroll on time.
You may not get Medicare until the next July and still pay penalties for life.

Real Example We See Often

Someone turns 65, is on COBRA, and thinks they’re covered.
They delay enrolling in Part B—then find out COBRA doesn’t count as credible coverage.

Now they’re:

• Facing lifetime Part B penalties
• Possibly owing Part D penalties
• Waiting months before coverage begins

This happens often—and it’s 100 percent avoidable.

How to Avoid This Mistake

Here’s how to protect yourself:

• Mark your calendar for the 7-month window around your 65th birthday
• Talk to an expert to review your current health coverage
• Make sure your coverage is through active employment with 20 or more employees
• Enroll 3 months before your birthday to avoid delays
• Don’t assume your current plan counts—get it in writing

Still not sure what counts as credible?
Give us a call and we’ll help you figure it out.

Wrap-Up

The Medicare Initial Enrollment Period is a key milestone—and it’s easy to misunderstand if you’re working, retired, or on another health plan.

Avoid the lifetime penalties. Avoid the delays. And get your coverage started the right way.

Call us at 800-208-4974 to book a free appointment.