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If you are covered under a group health plan at 65, you will not face a Medicare late enrollment penalty. That is true regardless of how large or small your employer is. The penalty protection comes from having group coverage, full stop.
But here is where people get hurt, and it happens more than you would think.
If your employer has fewer than 20 employees, Medicare is primary by law. That means your employer plan is designed to pay second, after Medicare pays its share. If you have not enrolled in Medicare, your small employer plan can legally process your claims as if Medicare already paid first. Since you never enrolled, Medicare paid nothing. Your employer plan covers only the leftover. You get the bill. (Verify with your employer – some small employers will make the exception to provide primary coverage)
No penalty. But potentially a very large out-of-pocket surprise at the worst possible moment.
The employer size question matters. The COBRA question matters. The spouse coverage question matters. And if you are still working past 65 with coverage through an employer of 20 or more, there is actually a smart way to handle all of it.
We built a free on-demand webinar that walks you through every scenario clearly and at your own pace. Visit Over20Medicare.com, watch it, and know exactly where you stand before you make any decisions.
Short, accurate, and drives the click. Want a Facebook version too?
Joanne Giardini-Russell is the founder and VP of Giardini Medicare, an independent Medicare insurance agency she started in 2018. Along with her son Cameron and a dedicated team, they have helped more than 8,500 clients across 24 states navigate the transition to Medicare. Their approach is education first — understand your options, then make a decision. She’s built a following of nearly 100,000 on TikTok by doing exactly that: making Medicare make sense. Reach Joanne at joanne@gmedicareteam.com or the team at 248-871-7756.
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