Retiring at 65—Your Medicare Checklist

Last Updated: June 2025 Print This Article

If you’re turning 65 and retiring within the next year, you’re in the right place. This checklist will help you prepare, enroll on time and avoid any gaps in your healthcare.

12–3 Months before turning 65:

Research your Medicare options.

  • Take time to understand Medicare and what it offers. Download Essence’s Medicare Starter Guide and explore our Learning Center for clear information on coverage options, enrollment timing and more.
  • Check with your employer’s benefits administrator to see if retiree coverage is offered, how long it lasts and whether enrolling in other plans affects your eligibility.
    • If your retiree benefits aren’t compatible with other Medicare coverage, such as a Medicare Advantage or Medicare Supplement (also known as Med Supp or Medigap) plan, it’s still wise to research those options, as they may provide better care and coverage for lower or similar costs.

Start planning.

  • Consider your health and lifestyle needs as they relate to healthcare. This will help you determine which Medicare plan may be the best fit.
    • Gather a list of your providers. Make sure they accept Medicare, and take note of which health system they’re part of. If you want to keep your current doctors, they will need to be in the network of the plan that you choose.
    • Determine your cost and budget preferences, for example, low-cost doctor visits, monthly premiums and whether maximum out-of-pocket protection is important to you.
    • Make a list of your prescriptions.
    • Decide if you need or want extras like, dental, vision, hearing, fitness or over-the-counter allowances.
  • Evaluate which plan option is right based on the information you gather:
    • Medicare Parts A, B and D
    • Parts A, B and D plus a Med Supp plan
    • Medicare Advantage plan
  • To avoid a tax penalty, you and your employer should stop contributing to your HSA six months before you retire.

3 Months before turning 65 to 3 months after:

Sign up for Medicare.

  • Sign up for Medicare Parts A and B during your Initial Enrollment Period (IEP), which starts three months before your 65th birthday month and ends three months after.
    • To enroll, contact Social Security at 1-800-772-1213 (TTY: 1-800-325-0778) from 8 a.m. to 7 p.m., Monday through Friday.
    • You’ll need your Medicare card to sign up for additional coverage.

Enroll in additional coverage.

  • During your IEP, you can also sign up for Part D prescription drug coverage and/or a Medicare Advantage (MA) plan. MA plans can provide your hospital, medical and prescription drug coverage and usually include extras like dental, vision and more.
  • When you’re 65, you’re able to sign up for a Med Supp plan, which can help with out-of-pocket costs associated with Parts A and B. Your six-month Medigap Open Enrollment Period starts the first day of the month you turn 65 and are enrolled in Part B. Med Supp plans don’t include prescription drug coverage and usually don’t include extras like dental and vision.

After 65:

Monitor plan changes yearly.

You have the opportunity each year during the Annual Enrollment Period (October 15 through December 7) to switch plans. Medicare.gov is a great resource for comparing your coverage options.

Have questions?

A licensed Essence Healthcare advisor can help you on your Medicare journey. Call 1-866-536-1052 (TTY: 711) from 8 a.m. to 8 p.m., seven days a week, to talk through your plan options and get answers to your questions. You can also attend a free Medicare seminar to help you understand your options.


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