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When Should I Enroll in Medicare?

  • dcafero
  • Jul 29
  • 2 min read

A Simple Guide for First-Timers 


Are you turning 65 soon? Then now is the time to start thinking about Medicare. For a lot of people, this is the first time dealing with new health insurance since leaving an employer-sponsored plan or private insurance. Enrolling in Medicare at the right time can help you avoid gaps in coverage or late penalties. Let's take a look at what you need to know to get started. 


You should enroll in Medicare during your Initial Enrollment Period (IEP).

When to Enroll 

You should enroll in Medicare during your Initial Enrollment Period (IEP). This is a seven-month window, beginning three months before your 65th birthday, includes your birthday month, and continues for three months after. 


For example, if your birthday is in July, your enrollment window opens in April and closes at the end of October. Enrolling early in your IEP ensures your coverage starts when you turn 65! 


If you are already receiving Social Security benefits when you turn 65, you will automatically be enrolled in Medicare Parts A and B. If you are not already receiving Social Security benefits, you’ll need to apply manually through the Social Security Administration. 


What If You’re Still Working? 

If you have health insurance through your employer, you may be able to delay enrolling in Part B without penalty. However, once your job or coverage ends, you then have a Special Enrollment Period to enroll in Medicare without facing a late fee that lasts eight months. 

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If you miss your IEP, you may have to wait for the General Enrollment Period (January 1 to March 31) and pay penalties. 


Planning ahead makes Medicare enrollment easier and helps ensure uninterrupted access to the healthcare you need. 

Start the enrollment process by contacting Medicare65forU for a complimentary consultation!

(203) 856-4237

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​​Medicare65forU is not affiliated with any government agency and we do not offer every plan available in your area. Currently we represent 6 companies and offer over 50 plans. Not all plans offer all benefits mentioned. Benefits may vary by carrier and location. Deductibles, copays, and coinsurance may apply. Limitations and exclusions may apply. $0 premium plans are not available in all areas. You must continue to pay your Part B Premium. A licensed insurance agent may contact you.

Donald Cafero, DBA, is a licensed agent CT #111279; NY #LA-676564

Please contact Medicare.gov, 1-800-Medicare, or your State Health Insurance Program (SHIP), to get information on all your options.

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