Medicare Timeline Series 3: Time to Enroll in Medicare

Hopefully, you’ve been keeping up with our “Timeline” series, and have a good idea about the kind of Medicare coverage you need, and you’re now ready to enroll.

If you haven't been keeping up with our timeline series, take a look at:


Enrolling in Original Medicare, or Parts A and B, doesn’t have to be complicated. In fact, it’s pretty easy. There are just a few things to keep in mind. Perhaps the most important thing to remember is that Medicare does have strict enrollment windows and deadlines. Unless otherwise eligible, your enrollment window begins three months before you turn 65 and extends through three months after. Signing up during this timeframe is critical to getting the best coverage options and avoiding potential penalties. If you miss your initial seven-month enrollment period, you can sign up for Original Medicare during the General Enrollment Period beginning January 1 and ending March 31, with your coverage beginning July 1. To join the four million others enrolling in Medicare this year simply:

  • Enroll online. To enroll in Medicare Parts A and B online, go to and fill out the application. According to, it should take no more than 10 minutes. If additional information is needed, the Social Security Administration will contact you directly. If not, you’ll receive your Medicare card in the mail.
  • Enroll at your local Social Security office. If you prefer to conduct your business in person, you can head to your local Social Security office and fill out the application there. The office will then process the paperwork and you’ll receive your official Medicare card in the mail.
  • Call the Social Security Administration. If you prefer, talk to a Social Security representative from the comfort of your home. Just call (800) 772-1231, and they’ll walk you through the enrollment process. 

Once you’ve signed up for Original Medicare, or Parts A and B, it’s time to sign up for a plan that covers what Original Medicare doesn’t. To recap, here are the three most common options:

  • Medicare Part C (Medicare Advantage) 
  • Medicare Part D 
  • Medicare Supplement Insurance (Medigap)

Similar to Original Medicare, it’s always best to sign up for additional coverage during the initial seven-month enrollment window. If you miss the initial enrollment, you can still sign up, but the timeframe varies for each option. Be sure to check with for exceptions.

  • Medicare Part C (Medicare Advantage): If you missed the seven-month Initial Enrollment Period, you can enroll between October 15 and December 7 of any year, during the Annual Enrollment Period. 
  • Medicare Part D: If you missed the seven-month Initial Enrollment Period, you can enroll between October 15 and December 7 of any year, during the Annual Enrollment Period. You may pay higher premiums by delaying. 
  • Medicare Supplement Insurance (Medigap): You can sign up at any time. But if you missed the six-month guaranteed enrollment period that begins when you sign up for Part B, you may be denied or charged more because of your health history

During any of these enrollment periods, you can sign up for additional coverage through a number of different resources. Here’s a list of the most common ways to enroll:

  • Contact the company directly. It’s not uncommon for people to shy away from this option because they feel companies are naturally biased and may not answer their questions honestly. If this is your concern, keep in mind that certain Medicare options, like Medicare Advantage plans, are heavily regulated by the government. These companies have no choice but to answer all questions honestly and limit any sales pitches. Because of this, contacting a company directly to ask questions and enroll is not a bad choice.
  • Contact an insurance broker. Generally brokers are used because they have a lot of options they can sell. When using a broker, remember that they may be working for a number of companies who are offering them various incentives. If a particular company appeals to you, lead the discussion and let them know that you already have a plan in mind, and always take what they say with a small grain of salt. If you have a trusted family member or friend who’s also a broker, that would be a good option.
  • Sign up online. Most plans now offer convenient online sign up with Q & A sessions and robust information on all their plans. Unless you have additional questions and prefer to speak to someone directly, online sign up is an easy way to enroll.
  • Sign up through If you’d rather not go through a broker or a company directly, you can always sign up for coverage on Medicare’s website,, by clicking “Find health & drug plans” in the green navigation tab. By putting in your zip code, you can view all the plan options in your area, select one and sign up on the spot.

If you pick a plan, and find out later that it’s not meeting your needs, you do have the option to change. You can generally add, drop or change your plan once a year from October 15 to December 7, though there are variations depending on the coverage option you choose:

  • Medicare Part D: You can add, drop or change your Part D coverage during Medicare Annual Enrollment. 
  • Medicare Part C (Medicare Advantage): You can join a Medicare Advantage plan or change your existing plan during Medicare Annual Enrollment. If you enroll in Medicare Advantage, you have until February 14 of the following year to change your mind. If you cancel your Medicare Advantage plan, you’ll be automatically enrolled in Medicare Parts A and B, and you can sign up for Part D.
  • Medicare Supplement Insurance (Medigap): You can add, change or cancel Medigap insurance at any time. 

Becoming one of the millions who sign up for Medicare each year is a great thing. By taking the time to research and pick an additional coverage option, you’re making your current and future health a priority. If you’re near 65, don’t wait to sign up! Start enjoying all the benefits Medicare has to offer by enrolling today.

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For more information on the BayCarePlus Medicare Advantage plan, visit