Losing Your Employer Health Coverage? Here's What to Do Next.
Moving from a group health plan to Medicare has a few deadlines that don't forgive mistakes. This free, plain-English guide walks you through the transition step by step—so you choose the right coverage instead of scrambling after your plan ends.
- The 8-month window to enroll in Part B—and why COBRA doesn't extend it
- Which "clocks" start when your group plan ends, and the order to handle them
- How to avoid a gap between employer insurance and Medicare
Cindy Kowalski · Licensed Independent Medicare Advisor · Licensed in 22 States
What's Inside
Everything you need to make the transition without a misstep.
- The Part B timing rules. Your 8-month Special Enrollment Period—and why COBRA and retiree coverage don't count as active employer coverage.
- The order of operations. Which decisions and deadlines come first when your group plan ends, so nothing slips.
- Supplement vs. Advantage at the transition. Why leaving employer coverage is often the moment you have the most freedom to choose either path.
- The Part D creditable-coverage rule. The quiet trigger for a late enrollment penalty that can follow you for as long as you have Part D coverage.
- How to avoid a coverage gap. Lining up your start date so you're never uninsured between plans.
- A simple transition checklist. A one-page timeline you can follow from "coverage ending" to "fully enrolled."
Who This Is For
If any of these sound like you, this guide was written for you.
Retiring after 65
You delayed Medicare because you had a group health plan, and now that plan is ending.
On COBRA or retiree coverage
You're covered for now, but you're not sure how it fits with Medicare—or when to act.
Coverage ending soon
You're still working, but your employer plan is changing or going away and you want a plan.
Why the timing matters more than most people realize
When your group coverage ends, several clocks start at once—and they don't all run the same length. Getting the order right protects both your wallet and your future choices.
Late penalties
Miss the Part B window and the penalty can follow you for as long as you have Part B coverage.
Harder to change later
Some choices are much more difficult to change later—the transition is when your options are widest.
Coverage gaps
Line the dates up wrong and you can be left briefly uninsured. The guide shows how to avoid it.
Who's Behind the Guide
I wrote this because I almost got my own transition wrong.
I nearly enrolled in the wrong Medicare coverage without knowing all of my choices—until my sister asked one question that changed everything. I built Eligry so people leaving employer coverage don't make that decision blind. As an independent advisor, I'll help you understand your Medicare options and how they fit your situation—education first, sales second.
- Independent Medicare Advisor
- Licensed in 22 States
- AHIP Certified
- No-Cost Medicare Reviews
Get the guide—then let's talk if you'd like.
The guide answers most questions on its own. When you want a second set of eyes on your specific timing, I'm a phone call away.
Or call (352) 464-4400 · Mon–Sat, 9am–6pm ET
I'm appointed with most major Medicare carriers, but my priority is helping you make the right decision. I'll explain every Medicare option available to you—even those I can't enroll you in—so you understand the complete picture before choosing a plan. My role is education first, sales second.
Not affiliated with or endorsed by the government or federal Medicare program.