Starting Medicare at 65

The year you turn 65 is a critical time for decisions that will impact your future health. Western Wind Insurance & Investments is here to help you understand when and how to enroll in Medicare.

Enrolling in Medicare the Year You Turn 65

Turning 65 is a significant milestone. One of the most important aspects of this age is starting Medicare, the federal health insurance program. Some people may be eligible before this due to certain health conditions or disabilities, but for many Americans, the year you turn 65 is when you first become eligible for Medicare. It’s essential to understand your options, deadlines, and available resources.

Initial Enrollment Period (IEP)


Your Medicare enrollment timeline depends on your age, work status, and current coverage. For most people, the first chance to sign up for Medicare:


  • Starts 3 months before your 65th birthday
  • Includes your birthday month
  • Ends 3 months after

This 7-month window is generally the best time to enroll in:


  • Part A (hospital insurance)
  • Part B (medical insurance)
  • Part C (Medicare Advantage)
  • Part D (drug plan) if not included in Part C

Important Notes

  • Enroll on time to avoid late penalties — especially for Part B and Part D.

  • Guaranteed issue rights during this initial enrollment window allow you to sign up for a Medigap plan without medical checks; once this right expires, you can face delays or higher costs based on health conditions if you want to join a Medicare Supplement plan.

  • You can sign up for Original Medicare (Parts A and B) through the Social Security Administration. Learn more about the process from Medicare.gov.

Still Working at 65?


If you have creditable employer coverage, you may wish to delay enrollment in Parts B and D without penalty. Once you retire or lose employer coverage, you’ll qualify for a Special Enrollment Period (SEP) and can enroll at that time. We can help confirm whether your employer coverage counts as “creditable.”


Automatic Enrollment for Social Security Recipients


If you’re already receiving Social Security benefits before age 65, in most cases you’ll be automatically enrolled in Medicare Parts A and B. Your Medicare card should arrive in the mail about three months before your 65th birthday.

Avoiding Late Enrollment Penalties

Some parts of Medicare carry lifetime penalties if you don’t sign up when first eligible.


  • Part B penalty: You’ll pay a 10% increase in your premium for every 12-month period you delay — unless you have creditable coverage.

  • Part D penalty: You’ll pay a 1% increase on the national base premium for every month you go without coverage, unless you have creditable drug coverage.

To avoid penalties, enroll as soon as you're eligible or confirm you’re covered by a qualified plan.

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Turning 65 Frequently Asked Questions

  • When should I start the enrollment process?

    Ideally, three months before your 65th birthday. That way your coverage starts on time and you avoid gaps or penalties.

  • Do I need to enroll in Medicare if I’m still working?

    Maybe. If your employer is a larger one (20 or more employees) and the health insurance they offer is considered “creditable,” you may delay enrollment in Part B and/or Part D. But if your company has fewer than 20 employees, then you will likely need to enroll in Medicare at 65. In this situation, Medicare is considered the primary payor, and your employer coverage is considered secondary.

  • How do I know if my drug plan is creditable?

    Your employer, VA, retiree plan, or union are required by CMS to provide written notice of creditable drug coverage each year. These letters should be sent out by October 15, before the start of the Medicare Annual Enrollment Period.

  • I’m already on Medicare. Do I need to do anything each year?

    It’s smart to review your Medicare Advantage or Part D plan each year with a licensed agent before the Annual Enrollment Period. Costs, coverage, and provider and pharmacy networks can change from year to year; we can help you decide whether to stick with your current plan or make changes. If you do nothing, your plan will automatically renew.

  • What if I miss my enrollment window?

    You may face penalties or delays in coverage. Contact us right away if you think you’ve missed it — we can help you look at your options and find out if you may qualify for a Special Enrollment Period.

  • What if my Medicare Advantage or Part D plan leaves Medicare?

    If your Medicare Advantage (Part C) or Medicare drug plan (Part D) is ending its contract with Medicare or exiting your service area, you should receive a notice from your plan by October 2, explaining your options. You will also receive a notice from CMS, which will tell you how to find other plans in your area. You’ll be granted a Special Enrollment Period (SEP) to choose a new Medicare Advantage or Part D plan or return to Original Medicare (and join a separate drug plan if needed). This SEP typically occurs just after the Annual Enrollment Period and lasts from December 8 to the last day of February.


    Note:


    • If your Medicare Advantage plan ends and you don’t make a change by December 31, you will be put in Original Medicare on January 1. In that case, you won’t have coverage for prescription drugs unless you enroll in a Part D plan.

    • The SEP gives you “guaranteed issue” rights to enroll in a Medigap plan without medical review, meaning existing conditions can’t be cause for higher premiums or denial of coverage. You have this guaranteed issue right for 63 days following the last day of enrollment in your Medicare Advantage plan.

    It’s important to review your options so you don’t have a gap in coverage. For help comparing plans, give us a call, visit Medicare.gov/plan-compare or call 1‑800‑MEDICARE.