Medicare Checklist

Turning 65 soon? Already 65 and losing your coverage through an employer or group? Make sure you’re ready to get the most out of your new Medicare benefits.

• Many Americans are automatically enrolled in Medicare Part A if they are already receiving Social Security benefits before age 65. If not, you will need to enroll yourself.
• You can choose to enroll in Medicare Part B (medical insurance) at that time; or you may be able to continue to receive benefits through your employer or group health insurance plan and enroll in Part B at a later date, depending on how many people are employed by your company.
• If you lose your employer coverage, you’ll typically have an 8-month Special Enrollment Period to enroll in Part B without penalty.

As your eligibility date approaches, we recommend you take the following steps:

Three months before your Medicare eligibility date:

• If you have active employer coverage, speak with your plan administrator to determine whether you should enroll in Part B. In general, employers with 20 or more employees allow you to delay Part B without penalty, but this depends on your specific plan.
• If you intend to take Medicare Part B benefits at this time, contact the Social Security Administration to enroll. You can enroll online through the Social Security Administration or by calling 1-800-772-1213.
• Contact TR Insurance Group. We are available to answer your questions and schedule a face-to-face or telephone appointment to discuss your Medicare insurance plan options.

One month before your Medicare eligibility date:

• Medicare Advantage and Part D enrollment depends on your Initial Enrollment Period (IEP) (7-month window).
• Check your new Medicare ID card and confirm the dates of your Part A and Part B coverages.
• If you are no longer keeping your pre-Medicare insurance, contact your health insurance company or your group plan administrator to cancel your coverage. Let us know if you’d like us to assist with your cancellation.

Every year thereafter, between October 15th and December 7th:

• Call us to review your coverage options for the new year. Medicare insurance plans change from year to year just like your medical needs do, so make sure you’ve still got the coverage that works best for you.

Updated April 30, 2026