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How to Talk with Social Security about Enrolling in Medicare


I turned 65 in March and called Social Security to discuss enrolling in Medicare.  I was given the wrong information from the agent over the phone which has now cost me the “famous” Part B penalty. Worst yet, I cannot enroll until after next January and my Medicare will not start until July 1, 2019.

I am now on the company’s COBRA plan vs company retiree medical because neither me or my wife does not have a Medicare card. The company’s retiree medical plan is now a Medicare Advantage plan and one must have Medicare Parts A and B to participate.

I am an educated person with a master’s degree, but Social Security overwhelmed me because when I called Social ‘s 800 number I received wrong advice.

After talking with the Toni Says® Medicare team, I now understand what I said was very wrong because I was not “working” full-time. I should have used the word “retirement”benefits instead of “company”benefits. Really didn’t know there was a difference.

Could you please share with those confused about enrolling in Medicare how to carry on a conversation with Social Security office to help one navigate the Social Security experience. Brian from Corsicana, TX

Thank You, Brian:

You are correct that knowing how to discuss your Medicare enrollment options with Social Security whether calling 1/800772-1213 or visiting your local Social Security office is vital to enrolling in Medicare properly and knowing what to do is extremely important.

Below are Social Security Medicare enrolling tips from Baby Boomer Society) when talking to Social Security and put control on your side.

  • Do:Put together a written plan regarding what you want to discuss regarding enrolling in Medicare whether you and your spouse are turning 65 either working full-time with or without employer benefits, turning 65 and no longer working with or without employer retiree benefits or past 65 and retiring with employer benefits.
  • Do: Call the Toni Says® Medicare help line to discuss your options for those who are simply too confused and distressed with what are the correct topics to discuss or words to say with the Social Security agent whether over the phone or in person at your local Social Security office. Toni Says® help line is 832/519-8664.
  • Do:When applying for Medicare Parts A and/or B when past 65, a full-time working employee and leaving company benefits, be sure to have a signed “Request for Employment” applications filled out for yourself and/or spouse and signed by your HR department with “Special Enrollment Period” written in red.
  • Do:Go directly to the local Social Security office in person.Be sure to wait in line to speak with a representative and process your Medicare paperwork directly with the specific Social Security office.  It is not advised to place paperwork in Social Security’s inside mail boxes or put in the mail.

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News and art, national and local. Began as alternative weekly in 1990 in Buffalo, NY. Publishing content online since 1996.

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