UNITED STATES—Dear Toni: I need your assistance to enroll in Medicare because I am past 65 and still working full-time with employer benefits.  Sherry, the office manager, from my cancer doctor’s office, said that the employer’s health plan denied the recent claim for my cancer treatment. The health plan considers it to be “experimental” and will not approve paying for this care.

The specific cancer treatment costs me over $15,000, which I had to pay on Friday from my 401k.  This amount will drain what I need for retiring.  To remain as a full-time employee, I am having to use my 12 weeks of vacation time for this cancer treatment and receive my full pay.

Sherry said her office currently has patients on Original Medicare with a Medicare Supplement that is paying for this cancer claim. She files their claims without a problem. Toni, I need to know how to begin my Medicare benefits as quickly as possible. Please advise me what I need to do. Thanks, Toni.– Brent from Nashville, Tenn.

Hello Brent: A health care professional advised me that many of the new cancer procedures are not approved by individual and employer group health insurance plans. The doctor said that these procedures are generally approved with “Original Medicare.”  He agreed with me that enrolling in Medicare past 65 and employed is complex, especially when an employee has the health issues you are currently experiencing, Brent.

Below are Medicare scenarios for enrolling in Original Medicare past 65, while employed and leaving employer benefits.  They are the same whether you’re still working, laid off or retiring:

  • Health issues are not covered by an employer health plan: You (or your spouse) are still working with health issues (like Brent), and the employer health insurance plan is not covering the doctor’s procedure. Even though you are not retiring, you need to enroll in Medicare.
  • Laid off: You (or your spouse) are laid off and need to enroll in Medicare.
  • Retiring past 65: You (or your spouse) decide to retire past 65 and need to enroll in Medicare.

The process to enroll in Medicare past 65 must be followed correctly, and is listed below:

  1. Two (2) Social Security forms to file: 1) Medicare Request for Employment Information (CMS-L564) must be signed by the employer’s human resource representative for you and/or your spouse covered by employer benefits. 2) Request for Enrollment in Medicare Part B (Medical Insurance) (CMS-40B) must be filled out and signed by you (and your spouse if they are also enrolling in Medicare). These two forms are available at the Social Security website (www.ssa.gov/forms).
  2. At the top each of these forms1) Request for Employment Information (CMS-L564) and Request for Enrollment in Medicare Part B (Medical Insurance)-(CMS-40B) form, it is very important to write “Special Enrollment Period” to inform the Social Security agent processing the form that you are signing up at the right time and prevent a Medicare Part B penalty. *If you have had two or more jobs since turning 65, then each of those companies must sign a CMS-L564 form.*
  3. Always make copies of your completed forms CMS-L564 and CMS-40B and be sure to write “Special Enrollment Period” at the top of each application.
  4. It is important to deliver the original forms to your local Social Security office especially when you want your Medicare to begin ASAP. There can be a delay in processing the forms when they are emailed or faxed. Keep your copies of the paperwork in case the paperwork is lost at the Social Security office.

Brent, as I have explained that there are options for enrolling in Medicare that many needing Medicare help are not aware exist. Because with Medicare, what you don’t know will HURT you!

Contact the Toni Says Medicare team at info@tonisays.com or call (832) 519-8664 for assistance or to answer Medicare questions. Sign up for the Toni Says newsletter at www.tonisays.com to download Toni’s new Medicare 2026 First Steps guide.