Working Past 65—Your Medicare Checklist

Last Updated: June 2025 Print This Article

Delaying retirement past 65? This checklist will help you navigate your Medicare options and ensure you have the right coverage while you keep working.

12–3 Months before turning 65:

Determine if you need Medicare’s hospital, medical or drug coverage.

  • If you’re covered under a group health plan, and your employer has 20 or more employees, you can delay Medicare without penalties. However, keep in mind that a Medicare plan might better meet your needs. See step 2 (Research your Medicare options …).
  • If your employer has fewer than 20 employees, you may need to enroll in Medicare Parts A (hospital) and B (medical) to avoid penalties.
  • Ask your benefits administrator if your employer-provided prescription drug coverage is creditable (considered as good as Medicare). If it’s not creditable, you may need to enroll in a Medicare Part D plan to avoid future penalties.
  • Check if your employer plan requires you to enroll in Medicare Parts A and/or B once you turn 65. If you’ve worked and paid Medicare taxes for at least 10 years, Part A is usually free. Part B does come with a monthly premium that can change each year.
  • Note that, if you have a Health Savings Account (HSA), enrolling in Part A will prevent you from making further HSA contributions. To avoid a tax penalty, you and your employer should stop contributing to your HSA six months before you retire.

Research Medicare options and compare against your employer coverage.

  • If your employer offers retiree benefits, find out if enrolling in other coverage will affect your ability to keep them.
  • Compare costs and benefits of your employer plan to Medicare plan options. A Medicare plan may offer better care and coverage for a lower monthly premium. You can learn more about your options in our Medicare Learning Center.

Understand Special Enrollment Period (SEP) rules.

  • When you retire after 65, you’ll have an eight-month Special Enrollment Period to sign up for Medicare without penalties.
  • Mark your calendar with your Medicare enrollment deadline based on when you plan to retire.

3 Months before turning 65 to 3 months after:

Sign up for Medicare.

  • If you’ve determined that you need or want to sign up for Medicare Parts A and B before you retire, you can do so during your Initial Enrollment Period (IEP), which starts three months before your 65th birthday month and ends three months after.
  • If you’ve delayed enrolling in Medicare Parts A, B or both, it’s best to sign up for them about a month before your employer coverage ends. This will help avoid a gap in your 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 Medicare Supplement plan (also known as Med Supp or Medigap), 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.
  • If you’ve delayed Medicare past 65 and are retiring, you’ll use your 8-month Special Enrollment Period to sign up for an MA or Med Supp plan.

After 65:

Monitor plan changes each year.

If you’re not ready to choose additional coverage, that’s OK. Remember to evaluate how your healthcare plan changes each year and compare it to your Medicare plan options. Medicare.gov is a great resource for comparing your coverage options.

A licensed Essence Healthcare advisor can also help you understand which plan might be the best fit. Call 1-866-536-1052 (TTY: 711) from 8 a.m. to 8 p.m., seven days a week, to talk through your options. †


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