How to Avoid Medicare Penalties When Working Past 65

How to Avoid Medicare Penalties When Working Past 65

Turning 65 is a major milestone — especially when it comes to health insurance. If you plan to stay on your employer’s health plan past age 65, it’s crucial to understand how to navigate Medicare enrollment rules to avoid costly penalties down the road.

Here’s what you need to know to avoid Medicare late enrollment penalties while continuing to work past age 65.

Understanding Medicare Parts and Potential Penalties

Medicare consists of several parts, and not all of them are mandatory at age 65. But delaying enrollment in certain parts without proper coverage can result in permanent financial penalties.

Do You Need to Enroll in Medicare at Age 65?

That depends on your current health insurance:

  • If your employer (or your spouse’s) has 20 or more employees, and you’re actively working, you can delay enrolling in Medicare Part B and D without penalty. The employer’s plan is considered creditable coverage, meaning it meets Medicare’s standards.
  • If the employer has fewer than 20 employees, you generally must enroll in Medicare when you turn 65. In this case, Medicare becomes your primary insurance, and delaying could lead to gaps in coverage and penalties.

When You Retire: Use the Special Enrollment Period (SEP)

Once you stop working or lose employer coverage (whichever happens first), you enter what Medicare calls a Special Enrollment Period. This allows you to sign up for Medicare without facing penalties.

  • You have 8 months to enroll in Part B after your employment or group coverage ends.
  • You have 63 days to enroll in Part D after your drug coverage ends.

Failing to enroll within these windows can trigger the penalties listed above.

Key Steps to Avoid Penalties

  1. Confirm Your Employer Coverage Is Creditable
    Talk to your HR or benefits administrator to confirm whether your current plan counts as creditable coverage for Medicare Parts B and D.
  • Creditable coveragemeans the employer health plan is at least as good as Medicare.
  • If your current employer coverageis creditable, you may be able to delay enrolling in Medicare Part B and/or Part D without penalties.
  • If it’snot creditable, you need to enroll in Medicare when first eligible to avoid penalties and coverage gaps.
  1. Gather the Required Paperwork
    When you retire and apply for Medicare Part B, you’ll need to submit Form CMS-L564 (Request for Employment Information), signed by your employer. This proves you had coverage and qualifies you for penalty-free late enrollment.
  2. Time Your Enrollment Carefully
    Enroll during your Special Enrollment Period instead of using the General Enrollment Period (January 1–March 31), which may result in a coverage gap and penalties. Also, COBRA isn’t considered group health plan coverage, so again, use the Special Enrollment Period!

Should You Enroll in Medicare Part A at 65?

Many people enroll in Medicare Part A at 65, even while working, because:

  • It’s free if you or your spouse worked and paid Medicare taxes for at least 10 years.
  • It can serve as secondary insurance to your employer plan.

However, if you have a Health Savings Account (HSA) and want to continue contributing to it, do not enroll in any part of Medicare, including Part A. Once you enroll, you can no longer contribute to your HSA.

Working past 65 doesn’t mean you’ll be penalized by Medicare — but it does require some proactive planning. By understanding your coverage, and acting during the correct enrollment windows, you can avoid costly mistakes and ensure a smooth transition when you’re ready to retire.

Go to www.medicare.gov for more information and download the Medicare and You handbook. These resources can answer many of your questions about enrolling for Medicare.

Cynthia Flannigan
Cynthia Flannigan
cynthia@mainstreetplanning.com

Cynthia made the shift to financial planning to guide clients through making good financial decisions through both grim and exciting changes in life. More than anything, she thrives on helping people. She obtained her CFP designation in 2008 and completed a masters in financial planning and taxation at Golden Gate University.

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