If you’re nearing age 65, you’ve probably heard something like this: “Don’t forget to sign up for Medicare, or you’ll get a penalty.” But what does that actually mean?
Medicare has specific enrollment windows—and missing them can lead to lifelong penalties. But whether or not you have to sign up at age 65 depends on a few key factors, including whether you’re still working and what type of coverage you have.
Let’s break it down.
The Medicare Initial Enrollment Period (IEP)
Your Initial Enrollment Period is the first time most people become eligible for Medicare. It’s a 7-month window that includes:
- 3 months before your 65th birthday month
- The month you turn 65
- 3 months after
Example: If your birthday is July 10, your IEP runs from April 1 through October 31.
What You Can Sign Up for During This Time
During your IEP, you can enroll in:
- Original Medicare Part A (hospital insurance)
- Original Medicare Part B (medical insurance)
- Part D (prescription drug coverage)
- Or a Medicare Advantage (Part C) plan that may include drug coverage
This is your ideal window to enroll penalty-free.
What If You’re Still Working at 65?
Here’s where it gets tricky. If you’re still working and have employer-based coverage, you may be able to delay enrolling in Medicare—but only if:
- Your employer has 20 or more employees (Medicare considers this creditable coverage)
- You’re actively working (not retired or on COBRA)
- Your drug coverage is considered creditable by Medicare standards
If those things are true, you can likely delay enrolling in Part B and Part D without a penalty.
But if you work for a company with fewer than 20 employees, Medicare becomes primary—and you do need to enroll when eligible to avoid penalties or denied claims.
Important note: COBRA and retiree coverage may not count as creditable for Medicare drug coverage. If you’re 65+ and on COBRA, you’ll typically need to sign up for Part D within 63 days of losing employer drug coverage to avoid a penalty.
What Happens If You Miss Your Initial Enrollment Period?
If you delay enrolling in Part B or Part D without creditable coverage, you could face:
- A late enrollment penalty added to your premium—for life
- A delay in coverage (you may have to wait until the General Enrollment Period)
- Unexpected medical bills because Medicare didn’t kick in when it should have
Other Enrollment Windows You Should Know
Special Enrollment Period (SEP)
If you delayed Medicare because you had creditable employer coverage, you get a Special Enrollment Period to enroll penalty-free once that coverage ends. You’ll have 8 months to enroll in Part B and 63 days for Part D.
General Enrollment Period (GEP)
If you missed your IEP and don’t qualify for a SEP, you can enroll during the GEP, which runs from January 1 to March 31, with coverage starting July 1. But late penalties will apply.
How to Know If It’s Time to Enroll
There’s no one-size-fits-all answer. It depends on:
- Your work status
- Your employer’s size and coverage
- Whether you’re on a spouse’s plan
- If you’re planning to retire soon
- Whether your drug plan is Medicare creditable
That’s why we always recommend talking with someone who knows how to apply these rules to your life—not just a generic chart online.
Need Help Figuring It Out? We’ve Got You.
At Brickhouse, we help people make Medicare decisions every day—and we slow down enough to actually listen. Whether you’re turning 65, still working, or helping a parent, we’ll walk you through it with clarity and confidence.
Click here to schedule a free consultation with Niki or a member of our team. There’s no cost and no obligation to enroll.
—
Written by Niki Feret
Licensed Independent Medicare Insurance Agent
Founder, Brickhouse Agency & Chicagoland Medicare
As a female agency owner in a space that’s often dominated by call centers and cookie-cutter advice, I started Brickhouse to do things differently.
We’re a boutique Medicare agency—real people helping real people. No scripts, no pressure, and no one-size-fits-all recommendations. Just thoughtful, personalized guidance that helps you make confident Medicare decisions.
If you’re ready to feel supported—not sold—
Schedule a free consultation here. There’s no cost and no obligation to enroll. Ever.