When Do I Have to Apply for Medicare if I’m Still Working?

Fact Checked

If you are an eligible, employed Medicare beneficiary who has group medical coverage, you may choose to delay Medicare enrollment. But Medicare could offer a cost savings – and if your employer has less than 20 employees, you’ll have no choice but to enroll. Consider these important timelines and regulations when you apply for Medicare while still employed.

When Am I Eligible for Medicare if I’m Still Working?

You are eligible for Medicare when you turn 65. But when you are still working and have employer-sponsored medical insurance, the decision when to apply is not always easy.

Learn about other instances in which you may qualify before age 65.

Your initial Medicare enrollment period is the seven-month timeline that spans:

  • Three months before your birthday month
  • The month of your birthday
  • The three months after your birthday month

If you don’t sign up for Medicare when you are first eligible and don’t have other medical coverage, you may go months without insurance.

The Medicare date on which you need to apply depends on if you have a current employer- sponsored medical plan. If your birthdate falls on the first of the month, then your Medicare date would actually be the first of the month prior.

How long you have to apply for Medicare depends on your current coverage as well as the number of employees at the company where you (or your spouse) work. This article will help you decide when and if you need to apply for Medicare when covered by an employer-based medical plan when you turn 65.

If your employer has 20+ employees If your employer has less than 20 employees
If you have group medical insurance from an employer you or your spouse are still working for after you turn 65, you can delay your Medicare date of enrollment until that employment ends or the coverage stops. Your employer coverage would be primary, as Medicare would be secondary.


You can still apply for Part A (Hospital) coverage. For most people there is no premium, but you can delay Part B (Medical) enrollment as you’d be paying monthly for Part B with little or no return for that coverage.


Once the employer medical coverage ends, you are entitled to a Special Enrollment Period for Medicare without any late enrollment penalties. To avoid a gap in coverage, apply for Medicare at least a month before your group coverage is ending.

If your company has under 20 employees, your Medicare enrollment takes place when you turn 65. Since Medicare is primary in this case, and employer coverage is secondary, if you don’t sign up for Medicare, you will not have proper coverage.


To ensure no gaps in coverage, you can apply for Medicare parts A and B three months before your 65th birthday. However, if you have already been drawing Social Security benefits for at least four months before you turn 65, you’ll automatically be signed up for Medicare Part A and Part B. The Part B premium will be deducted from your Social Security benefit each month.

Do You Have to Switch to Medicare From Your Employer’s Plan?

Some laws prohibit employers with over 20 employees from requiring Medicare-eligible employees to sign up for Medicare and drop the employer plan. But those laws do not apply to places that employ fewer than 20 people.

At those companies with under 20 employees, the employer can decide, but it’s usually beneficial for those Medicare-eligible employees to enroll in Medicare.

There’s no need to double up on coverage, especially if you are paying multiple premiums. You can compare what you are paying for group health coverage and what your benefits look like under that plan versus what you would pay under Medicare. You might even find that signing up for Medicare at 65 may make the most financial sense in any situation reviewed above.

What Is Your Medicare Special Enrollment Period?

If you have delayed Medicare Part B enrollment due to being on an employer plan, once you leave your employer, you’ll have an eight-month Special Enrollment Period to sign up for Medicare. This Special Enrollment Period will start the month after you leave employment, or the month after your group health coverage ends, whichever happens sooner.

You will not be assessed any late enrollment penalties if you sign up during this time period. This eight-month special enrollment period is also available if you are covered under your spouse’s employer plan.

Once you are enrolled in Medicare coverage, you will have the chance to review and change your Medicare plans each fall during Medicare open enrollment, which is the Annual Enrollment Period (AEP). Changes made during this period from Oct. 15 through Dec. 7 take effect the following year on Jan. 1.

Can You Keep Your Health Savings Account With Medicare?

A Health Savings Account (HSA) is used to pay for medical expenses with pretax funds. There are certain requirements you need to meet to be able to contribute to an HSA.

You must be enrolled in a high-deductible health plan and you can’t have any other plan. Since Medicare is considered another health plan, you can no longer contribute funds to an HSA once enrolled in Medicare. If your employer was contributing on your behalf, they would also have to cease those additions.

You may receive a tax penalty on funds you contribute to an HSA after you are enrolled in Medicare. However, you don’t lose those funds in your HSA account, as you can use them to pay for expenses such as Medicare premiums, copayments, deductibles, and future health care costs.

Medicare Consultant

Michele Dubbert is a licensed independent health insurance agent, working with individuals, families and small businesses. She has been in the Health Insurance industry since 2013. Her passion and specialty prevail in Medicare as she truly enjoys working with this age group.

She takes joy in learning about her clients and their needs. This assists in finding the right plan that fits their lifestyles and most importantly gives them piece of mind. Many of her clients come to her frustrated with the Medicare process, so she helps them from beginning to end.

Being a broker for many carriers allows her to offer her clients a wide range of coverage options. Her office is based in Fort Collins, CO, but serves all of Colorado. She continues to further her experience with trainings and education and is expanding to additional service states.

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