Medicare Enrollment Process: What to Do and When

Enrolling in Medicare involves a few key steps, and the right approach depends on your situation. Understanding what to do—and when to do it—can help you avoid delays, coverage gaps, or penalties.


At Croft Insurance Services, Inc., we guide individuals throughout Bedford, Lynchburg, Roanoke, and surrounding Virginia communities through the Medicare enrollment process so they can move forward with clarity.



It’s important to note that Social Security manages Medicare enrollment, not insurance companies. Our role is to help you understand your options and make informed decisions before and after you enroll.

Speak with a licensed agent and receive personalized guidance for your coverage options.

Situation 1: Turning 65 and Already Receiving Social Security


If you are already receiving Social Security benefits when you turn 65, you will typically be automatically enrolled in Medicare Parts A and B.

Your Medicare card will be mailed to you about three months before your 65th birthday. In most cases, no additional action is required.

However, this is still an important time to review your coverage options, including whether you need additional coverage such as a Medicare Advantage plan, Medicare Supplement, or Part D prescription drug plan.


Situation 2: Turning 65 and Not Yet Receiving Social Security


If you are not receiving Social Security benefits, you will need to actively enroll in Medicare.


You can do this by contacting Social Security or applying online.


For local assistance:

  • Lynchburg area: (866) 964-6142
  • Roanoke area: (866) 701-8179


You can also apply online at www.ssa.gov.


To complete your enrollment:

  • Create a Social Security (SSA) account
  • Apply for Medicare Parts A and B
  • Decide whether you want to begin receiving Social Security benefits at the same time


Once your enrollment is processed, you can move forward with selecting additional coverage based on your needs.


Situation 3: Over 65 and Enrolling in Part B


If you delayed Medicare Part B because you had qualifying employer coverage, you can enroll later using a Special Enrollment Period.


To do this, you will need to complete and submit the following forms:

  • CMS-40B (Application for Enrollment in Part B)
  • CMS-L564 (Request for Employment Information)


These forms confirm that you had qualifying coverage and allow you to enroll without penalty.


Completed forms are typically submitted to Social Security prior to your desired coverage start date.


For local processing:

  • Lynchburg fax: 833-650-2284
  • Roanoke fax: 833-912-2328


What Happens After You Enroll?


Once you are enrolled in Medicare Parts A and B, the next step is choosing how you want your coverage to work.


This may include:

  • Medicare Advantage plans
  • Medicare Supplement (Medigap) plans
  • Prescription Drug Plans (Part D)



Each option works differently, and your decision should be based on your healthcare needs, provider preferences, and budget.

Get Help Before You Enroll


Before submitting your Medicare application, it’s often helpful to review your options so you can make informed decisions from the start.


Croft Insurance Services, Inc. provides local, personalized guidance to help you understand your coverage choices and avoid common mistakes.



We are based in Bedford and serve clients throughout Central and Southwest Virginia.