WARNING: Miss Your 8-Month Window and Medicare Adds a Penalty to Every Part B Bill for the Rest of Your Life

Dear friend,

You did everything right. You kept working past 65. You kept your employer's health plan. You didn't need Part B yet.

Now you're retiring, and suddenly there are two government forms standing between you and your Medicare: Form CMS-40B, which you fill in, and Form CMS-L564, which your employer has to fill in and sign.

Then the trouble starts. HR has never seen an L564. Or they fill in Section B wrong. Or the company was sold and nobody knows who should sign.

Sound familiar?

Here's what's at stake. You have 8 months from the month your job or your employer coverage ends, whichever comes first. Miss it, and you may have to wait for the General Enrollment Period (January 1 to March 31), go months without Part B, and pay a late penalty.

And that penalty doesn't go away. It's 10% of the Part B premium for every full year you were late, for as long as you have Medicare.

Most people who get caught didn't do anything careless. They just didn't know:

• That the 8 months start when the job or the coverage ends, whichever is first.
• That COBRA and retiree coverage don't count as coverage from current work.
• What to send when the employer won't or can't sign the L564.
• Exactly what Section B should say, so Social Security doesn't send it back.

That's why we made this kit.

Introducing the Part B Late Enrollment Kit

Filled-in examples of Forms CMS-40B and CMS-L564, plus a plan for when your old employer is slow, gone, or won't sign.

• Filled CMS-40B exampleEvery field filled for someone who worked past 65, with notes on the boxes people get wrong.
• Filled CMS-L564 example for your employerHand it to HR with Section B already explained, so they sign it right the first time.
• If your employer won't sign or is goneThe other proof Social Security accepts: W-2s, pay stubs, insurance cards, and how to present them.
• 8-month deadline worksheetFind your exact Special Enrollment Period end date, so you don't miss it by a week.
• Ready-to-sign cover letterOne page that tells Social Security what you're sending and why you qualify.
• How to submit: online, by fax, or by mailStep by step for each route, and how to confirm it arrived.

Here's a look inside

Plus 3 free bonuses

Included with every copy, at no extra cost:

"The forms are free. Why pay $39?"

They are free, and we'll show you where to get them. You're not paying for the forms. You're paying for filled-in examples and a plan, so the forms are accepted the first time and your deadline doesn't slip away while you go back and forth.

Every full year of delay adds $20.29 a month to your Part B bill in 2026, for life. The kit costs $39, once.

"My HR department will handle it."

Maybe. But many HR departments see this form once every few years. The kit includes a ready-to-send letter that tells them exactly what to fill in, so you're not relying on them to figure it out.

Questions before you buy