Who can help fix a serious Medicare enrollment issue?
Dear Toni: On Nov. 6, when the government was still shut down, I turned in my Medicare enrollment forms signed by my employer to the local Social Security office. I never received anything from Social Security about being enrolled, so I went back to the office and found out that my paperwork was lost. I refiled a copy of the forms with Social Security about three weeks ago, and now my Social Security fun begins.
I must fight Social Security because they are under the impression that I have waited past my eight-month window to enroll in Medicare Part B, which I did not. I am now receiving a Part B penalty. What a nightmare!
Can you please explain what I should do to appeal this Medicare decision? — Nick, San Antonio
Dear Nick: If you need help rectifying your Social Security and Medicare issues, contact your congressional office. Visit their website for the local office contact information, or you can email them from the congressional website.
The 2026 “Medicare & You” handbook explains the rules of leaving employer’s benefits when you are still working past age 65. It discusses the special eight-month window for enrolling in Medicare and spells out that this period begins the month after employment ends or health coverage ends, whichever happens first.
Nick, when you enrolled with Social Security, you might have been close to the end of the eight-month window, so explain this to your congressional office’s agent when you contact them.
Here are a few of the Social Security forms used for Medicare (don’t forget to write “Special Enrollment Period” in red at the top of these forms to avoid receiving a penalty when submitting them to your local Social Security office whether in person or by email):
CMS-L564, Request for Employer Benefits: This form that shows proof of employer health benefits from the specific employer. If you have had two or more employers since turning 65, have a CMS-L564 form signed by each employer to turn in to Social Security when applying for Medicare Part B (medical insurance).
CMS-40B is the Application for Enrollment in Medicare Part B: Attach this form to the CMS-L564 when applying for Part B after leaving employer benefits past age 65 and 90 days.
SSA-44, Medicare Income-Related Monthly Adjusted Amount — Life-Changing Event: This one advises Social Security of a major life-changing event that has lowered your income. Life-changing events include marriage, divorce, death of a spouse, work stoppage or reduced hours and loss of property.
Nick, search for documents and evidence to prove that you did not wait past the eight-month window to apply for Medicare after leaving employer benefits. Have them ready to show or send to a representative from your congressional office or local Social Security office.
Readers, remember to always have Part B in place when leaving your job or losing company benefits. There might not be a second chance.
Toni King is an author and columnist on Medicare and health insurance issues. If you have a Medicare question, email info@tonisays.com or call 832-519-8664.





