A senior man working at a laptop.

In America today, it is common for seniors to continue working beyond turning 65, which is also when you become eligible to enroll in Medicare. Oftentimes, I am asked “when should I enroll in Medicare?” and the answer is “it depends.”

When you should enroll in Medicare depends on a number of factors.

  • Whether you plan to keep working past 65
  • The size of your employer
  • Whether you’re enrolled in an employer group health insurance plan
  • Whether you and/or your employer are contributing to a Health Savings Account (HSA)

Read on for more information on enrolling in Medicare and working past 65.

An elderly couple riding bikes together.
If You Plan to Retire at 65, Enroll in Medicare During Your IEP

The government agency charged with the responsibility of administering Medicare is the Center for Medicare and Medicaid Services (CMS). CMS rules are very clear when you should enroll in Medicare Part A and Part B if you plan on retiring from work when you reach age 65.

In order to avoid a Part B late enrollment penalty, in this situation, you should enroll in Part A and Part B of Medicare during your Initial Enrollment Period (IEP), which is the seven-month period that begins three months prior to the month you reach age 65 and ends three months after the month you reach age 65.

The penalty for late enrollment in Part B is two-fold.

  1. The Part B monthly premium will be increased 10% for each year beyond age 65 that you fail to enroll in Part B. This penalty increase is not one-time only. You will have a 10% increase on your Part B premium each year.
  2. When you choose to enroll late, you are permitted to enroll during the General Enrollment Period only (Jan 1 thru March 31) and the effective date will be July 1 following your request for enrollment.

There is no penalty for delaying enrollment in Part A because there is no premium for Part A, unless you do not qualify for premium free Part A. This exception is extremely rare, so if you have questions, please reach out to Florida Medicare Specialists directly.

If you’re planning to retire by the time you turn 65, there’s no reason you shouldn’t enroll in Medicare Parts A and B (Original Medicare) during your IEP.

When to Enroll In Medicare If You Plan to Work Past 65

If you won’t be retiring when you turn 65, when you should enroll in Medicare depends greatly on the size of your employer and the health care plan you already have in place.

If You Have Health Insurance Through Your Employer

If your employer offers a group health insurance plan and has more than 20 employees, you can delay your Original Medicare IEP without incurring any late-enrollment penalties. This also applies if you are listed as a dependent on your spouse’s employer group health plan.

In this situation, whenever the time comes that you are no longer enrolled in an employer group health plan, whether through your employment or through your spouse’s employment, you MUST enroll in Part A and Part B within 60 days of losing that coverage to avoid late enrollment penalties.

At that time you will also be required to prove the period beyond reaching age 65 that you were enrolled in an employer group health plan.

However, if you are still working past 65 and your employer has more than 20 employees but you choose NOT to enroll in your employer’s group health plan, you should enroll in Medicare during your IEP.

If your employer has fewer than 20 employees, you will need to enroll in Original Medicare during your IEP around your 65th birthday to avoid penalties, as the same exceptions will not apply.


If You and/or Your Employer Contribute to an HSA

Internal Revenue Service regulations require that you and/or your employer cannot make a contribution to an HSA while enrolled in any healthcare plan other than a High Deductible HealthCare Plan.

Since Medicare Part A or Part B meet the definition of “other healthcare plan,” you and/or your employer should stop contributions to an HSA six months prior to enrolling in Part A or Part B. Failure to follow this rule may (and probably will) result in tax penalties.

If you and/or your employer are contributing to an HSA, it is imperative that you seek guidance from your employer’s HR or Benefits Department.

An elderly woman consulting a coworker at her office.
Contact Florida Medicare Specialists for Guidance

Because of varying rules affecting many parts of Medicare, understanding when to enroll in Medicare can be difficult. It is important for you to also understand that any misunderstanding of these rules will always be your fault. Governmental agencies are never at fault.

That’s why I’m here.

If you’re unsure when you’ll be retiring and don’t know how that will affect your Medicare Enrollment, contact Florida Medicare Specialists for help with the process. We have more than 45 years of experience in Florida insurance and have worked exclusively in Medicare since 2009.

We do not charge a fee for our services. We’re here to help you understand your options so you can make the best choice for your future.

As a dedicated health insurance expert for 46 years (with 12 years focused only on Medicare) in The Sunshine State, Ken Brown is passionate about educating people on the intricacies of health coverage for Florida’s seniors.

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