Retiring Soon?

Your Smooth Transition from Employer Coverage to Medicare

Your "Next Chapter" Starter Kid

You've spent years under an employer's plan. Moving to Medicre is a major shift, but it doesn't have to be a confusing one. Based on your results so far, we'll help you bridg the gap between "Active Employee" and "Medicare Beneficiari" without the common mistakes that catch some retirees off guard.

Medicare Myths vs. The Hard Truth

Don't let water-cooler advice cost you money in permanent penalties.

THE MYTH

"I'm taking COBRA, so I don't need to sign up for Medicare Part B yet."
"I have 8 months after my COBRA ends to get Medicare without penalty."
"My employer's retiree plan counts as creditable coverage for Part B."

Employment & Health

COBRA is NOT creditable coverage. Medicare requires you to sign up for Part B within 8 months of leaving unemployment — not when COBRA ends.
Wait too long, and you'll face a 10% lifetime penalty for every year you delayed Part B while on COBRA.
Retiree coverage is secondary to Medicare. If you don't have Part B, your retiree plan can legally refures to pay their portion of your bills.

UNDERSTANDING COBRA TIMING

COBRA is a valuable tool that allows you to keep your employer's insurance temporarily after leaving your job. However, it's important to understand how it interacts with Medicare enrollment to avoid permanent premium increases.

The Enrollment Timeline
While COBRA provides health coverage, Medicare does not consider it "active employment" coverage. Your 8-month Special Enrollment Period (SEP) for Part B begins the month your employment ends, regardless of how long your COBRA coverage lasts.

What To Know About Your Special Enrollment Period

What is a Special Enrollment Period (SEP?)

A Special Enrollment Period is a designated window where you can sign up for Medicare without penalty, even if you are outside your initial 65th birthday window. Retiring and losing employer coverage is the most common Qualifying Life Event.
1
The Timeline: You have an 8-month window to sign up for Part B, starting the month after your employment or your health coverage ends (whichever happens first).
2
The Benefit: Using an SEP means no late-enrollment penalties and no gap in coverage between your job and your new Medicare plan.

Necessary Paperwork

To prove you had creditable coverage, you'll need two specific forms from the SSA:

  • CMS-40B: Your application for Part B
  • CMS-L564: Completed by your employer to prove you had insurance.
Download CMS-40B
Download CMS-L564

You're Retiring — Here's How We Can help

Original Medicare is a great start, but it doesn't help you cover everything. SmartMatch can help you decide which Medicare path to take — Medicare Supplement or Medicare Advantage.
Connect With SmartMatch
1-888-411-7647 | TTY: 711

Which type of Medicare insurance is right for me?

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