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Don’t Make These 3 Mistakes That Can Mess Up Your Medicare Enrollment

If your time for Medicare enrollment is approaching, just imagine being shut out when you try. That’s a real possibility and it happens more frequently than it should. Here’s a real-life, sad story.

Helena’s 65th birthday came in August 2020. When she tried to enroll in mid-November (the last month of her Initial Enrollment Period (IEP)), she was locked out with no time to correct the situation. 

Helena committed three mistakes that wreaked havoc on her enrollment. Now, you can learn from her story.

1. Waiting until the last minute

Medicare is intimidating. Some keep putting it off, just as they might do with a root canal. In the past, they would rush down to their local Social Security office at the last minute and everything would be fine. 

However, since March 17, 2020, all local Social Security offices have been closed to the public. Even before that, years of budget cuts have led to long waits for customer service. One client said he was on hold with Social Security for almost 75 minutes, only to be disconnected before he spoke to anyone. 


Helena made a mistake when she kept postponing enrollment. Don’t be like her; take the necessary steps as soon as you are eligible. 

  • Those turning 65 who will need Medicare should enroll during the first month of their Initial Enrollment Period (IEP). Helena could have started the process in May. 
  • Those over 65 who are retiring should start the process three months before the retirement date. Medicare allows them to specify the effective date for Medicare so coverage can be in place the first month of retirement.
  • Those who missed their chance to enroll should take action in early January, the first month of the General Enrollment Period

2. Not having a my Social Security account

Before the pandemic, there were three ways to enroll in Medicare: visit the local office, make a phone appointment or enroll online. I was amazed at the number who would choose to visit their local office and wait for their turn. 

With closed offices and phone appointments almost impossible to get, the only reliable option is online enrollment through a my Social Security account. 

Helena’s mistake was not having an account. Don’t be like her; create an account through the Social Security website. You can do this at any time, even if Medicare is not on the horizon. 

To set up an account, you must:

  • be at least 18 years old 
  • have a Social Security number, and
  • have a valid US mailing address and an email address. 

If you have problems, establishing your account, contact Social Security at (800) 772-1213.. 

If you already have an account, take a few minutes to log in and make sure you can access it successfully. Social Security has procedures for retrieving or changing username and password.

FYI: A freeze on your credit report could also create problems establishing a my Social Security. Read more here.

3. Failing to notify Social Security about changes in name and address

During the process of establishing a my Social Security account, the government will verify information in its system against the information you submit. This was likely the reason Helena missed her deadline. After the system locked her, it took considerable effort to connect with a Social Security agent. Finally, she learned that her current name did not match the one in Social Security’s records. After her divorce in 2009, Helena changed her name.

When legally changing a name because of marriage, divorce, or other reasons, one must notify Social Security and get an updated card. The first step is for Social Security to see the required original documents. (Social Security cannot accept photocopies or notarized copies.) If Helena had done this in 2009, she could have taken the documents to her local office, shown them to an agent, and then carried them back home. Now 12 years later, Helena not only had to find the documents but send them, hoping nothing would go wrong. 

As you suspect, Helena was not able to enroll in November. Because she missed her IEP, she enrolled in January, the General Enrollment Period, and her coverage will begin July 1.

Don’t make Helena’s mistake. Notify Social Security of changes in name and address.

Medicare enrollment is a very important life event. You don’t want to make mistakes that will haunt you forever. But, given the complexity of today’s Medicare, with its various timelines, different options and multitudes of plans, mistakes can happen. By starting the process early, setting up a my Social Security account, and making sure information is up-to-date and accurate, you’ll avoid three of the most damaging mistakes.

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