Employment & Medicare

Medicare Benefits for Those
Who Are 65 & Still Working

There are many things to consider when you are still working and on your employer’s health insurance. I will explain how it works, review your options, and together we can decide the best strategy for the remainder of your working years.

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Get guidance on the first steps to explore your Medicare options.

Understand your choices and how employer coverage may impact enrollment.

Learn the enrollment process, timelines, and important information.

Compare Medicare coverage choices to find the right fit for you.

Get clarity on Medicare costs and how to plan for your healthcare expenses.

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What to do when you are working and eligible for Medicare?

If you are still working with employer coverage when you turn 65, you first need to decide whether keeping your current job-based health insurance or transitioning to Medicare makes the best financial and medical sense for your situation. Though reaching age 65 while actively working puts you in a unique position,  you aren't automatically required to sign up for Medicare unless your company has less then 20 employees. As such, your very first move should be to check how many people work at your company.

The Rule of 20

  • 20 or More Employees: If your business has 20 or more employees, your employer plan stays primary, which gives you the green light to delay enrolling in Medicare Part B without worrying about late-enrollment penalties down the road.

  • Less then 20 Employees: On the flip side, if your company employs fewer than 20 people, you must take Medicare. In this case, Medicare becomes your primary coverage and your company insurance becomes secondary. In those smaller group settings, skipping Medicare enrollment when you turn 65 can leave you facing massive out-of-pocket bills (because your work policy expects Medicare to pay its share first)  and potential penalties down the road. 

  • 20 or more employees, case where Medicare may still be a better option: Even if you work for a large company and can stay on your job-based plan, it pays to run the numbers. Group health insurance isn't always the cheapest option anymore. Take a close look at what you pay out of your paycheck every month, along with your annual deductible and doctor copays, and stack that up against a tailored Medicare package. One crucial trap to watch out for involves Health Savings Accounts: as soon as you sign up for any portion of Medicare—even premium-free Part A—you can no longer make pre-tax contributions to an HSA. Taking a few minutes to evaluate your total health expenses and tax setup now will help you avoid frustrating surprises later.

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Action Steps: to decide whether to go onto Medicare when you turn 65

  • Evaluate size of company you work for(The rule of 20)

  • If more then 20, do a cost/benefit analysis evaluating whether going on Medicare or staying with your work employer is the better option

  • If you decide to STAY with employer Insurance, enrolling in Part A (only) is optional, but recommended. Its one step less that you have to do later once you officially drop your employer insurance or retire.

  • If you choose Medicare, research Secondary Plan Options  & Drug Plans. Make sure to Enroll before your Part B effective date so . find a broker like us or choose to do it on your own.

Commonly Asked Questions About Employer Health Insurance & Medicare

Do I need Medicare Part B if I have Employer Health Insurance?

Whether you need Medicare Part B when you have employer health insurance depends on various factors, such as the size of your employer and the type of coverage they offer. Here are some general guidelines:

1. Employer Size: If you work for an employer with 20 or more employees, your employer’s health insurance plan is considered primary, and Medicare is secondary. In this case, you may delay enrolling in Medicare Part B without facing penalties as long as you have credible coverage through your employer.

2. Employer Coverage: If your employer’s health insurance is comprehensive and meets Medicare’s standards for creditable coverage, you may not need to enroll in Part B immediately. However, it’s essential to check with your benefits administrator to ensure your coverage meets Medicare’s requirements.

Part-Time Work: If you have health insurance through an employer where you work part-time, Medicare may be your primary coverage, and you might need to enroll in Part B when you become eligible.

Retirement: When you retire or lose your employer coverage, you generally have a Special Enrollment Period (SEP) during which you can sign up for Medicare Part B without penalty.

It’s crucial to understand your specific situation and consider factors such as the cost, coverage, and timing of enrollment in Medicare Part B. You may want to consult with a Medicare advisor (such as myself) or your employer’s benefits coordinator to make an informed decision.

Is Employer Health Insurance Primary over Medicare?

Yes, in most cases, employer health insurance is considered primary over Medicare. This means that if you have both employer health insurance and Medicare coverage, your employer’s plan pays your medical bills first, and Medicare may pay some or all of the remaining costs, depending on the specific circumstances.

However, there are exceptions to this general rule, such as if you work for a small employer with fewer than 20 employees, in which case Medicare may be primary. It’s essential to understand your specific situation and how your employer’s health insurance interacts with Medicare.

If you have questions about whether your employer’s health insurance is primary or secondary to Medicare, it’s a good idea to check with your employer’s benefits administrator or with Medicare directly for clarification.

How Does Medicare Work with Other Insurance?

Medicare works with other insurance in various ways, depending on the type of coverage you have. Here’s a general overview:
1. Employer Health Insurance: As stated above, if you have health insurance through your or your spouse’s current employer and the employer has 20 or more employees, the employer’s insurance is typically primary, and Medicare is secondary. This means that your employer’s plan pays your medical bills first, and Medicare may pay some or all of the remaining costs. If you have retiree health benefits from a former employer, Medicare may coordinate with that coverage as well.

2. Medicaid: If you’re eligible for both Medicare and Medicaid, Medicaid may help pay for costs that Medicare doesn’t cover, such as copayments, deductibles, and premiums.

3. Medicare Supplement Insurance (Medigap): If you have a Medigap policy, it helps pay for some Medicare costs, such as copayments, coinsurance, and deductibles. Medigap policies work with Original Medicare.

4. Medicare Advantage Plans (Part C): These plans provide all your Medicare Part A and Part B coverage and often include additional benefits, such as prescription drug coverage (Part D), dental, vision, and hearing benefits.

5. Veterans Benefits: If you’re a veteran receiving VA benefits, you can use both VA benefits and Medicare. They generally do not coordinate benefits, but you can use them together to get additional coverage.

6. TRICARE: If you have TRICARE, it typically works with Medicare. TRICARE for Life acts as a supplement to Medicare, covering expenses that Medicare doesn’t cover.

It’s essential to understand how your various insurance plans work together to ensure you get the most coverage and benefits. If you have questions about how Medicare coordinates with your other insurance, you can contact a Medicare Advisor like myself, Medicare, or your insurance providers for more information.

What happens if you don't enroll in Medicare at 65?

If you don’t enroll in Medicare at age 65 and you’re eligible, you may face penalties or gaps in coverage depending on your circumstances:

Late Enrollment Penalties: If you don’t sign up for Medicare Part B (and, if applicable, Part D or a Medicare Advantage plan) when you’re first eligible at age 65, you may incur a late enrollment penalty. This penalty typically results in a permanent increase in your monthly premium for Part B and, if applicable, Part D coverage.

Coverage Gaps: If you delay enrolling in Medicare, you may have gaps in coverage if you’re not covered by another health insurance plan. This could leave you responsible for paying out-of-pocket for medical expenses until you enroll in Medicare.

Similarly, by not enrolling in Medicare when you’re first eligible, you may be subject to late enrollment penalties described above.

Limited Enrollment Periods: If you miss your initial enrollment period when you turn 65, you’ll have to wait for the General Enrollment Period (January 1 – March 31 each year) to sign up for Medicare Part A and/or Part B. Coverage will start July 1 of that year, and you may still incur late enrollment penalties.

However, there are some exceptions to these penalties and coverage gaps, such as if you have coverage through an employer with 20 or more employees, in which case you may be able to delay enrolling in Medicare without penalties until you retire or lose your employer coverage.

It’s essential to understand your Medicare eligibility and enrollment deadlines to avoid penalties and ensure you have the health coverage you need when you need it.

Can I delay Medicare Part B if I am still working? Y

Yes, you can delay enrolling in Medicare Part B if you’re still working and have health insurance through your employer or your spouse’s employer, provided that the employer has 20 or more employees. In this case, your employer’s group health plan is considered primary, and Medicare would be secondary.

If you’re eligible for premium-free Medicare Part A (which covers hospital stays), you may enroll in Part A without enrolling in Part B. However, if you delay enrolling in Part B because you have employer coverage, you’ll qualify for a Special Enrollment Period (SEP) to enroll in Part B when your employer coverage ends or when you decide to retire.

When exactly should I start my Medicare paperwork?

Your main sign-up window is called the Initial Enrollment Period (IEP), which spans 7 months. It opens 3 months before your 65th birthday month, runs through your birth month, and closes 3 months after. To make sure your coverage kicks in on the very first day of the month you turn 65, aim to complete your enrollment during those first 3 months.

Will Medicare automatically start when I turn 65?

Only if you are already collecting Social Security benefits. If you currently receive retirement checks, Social Security will automatically enroll you in Parts A and B and mail your card roughly 3 months before your birthday. If you haven't claimed Social Security yet, Medicare won't start on its own—you will need to submit an active application through Social Security.

I plan to keep working past 65. Do I still need to enroll?

That depends entirely on the size of your company. If your employer has 20 or more full-time staff, your group health insurance acts as your main coverage, allowing you to delay Medicare Part B without incurring penalties. If your employer has fewer than 20 staff members, Medicare becomes your primary payer. In that scenario, signing up for Parts A and B at 65 is essential to prevent massive coverage gaps.

What should I budget for Medicare coverage?

Most people pay $0 per month for Part A, provided they or their spouse paid Medicare taxes for at least 10 years (40 quarters). Part B has a standard monthly premium set by the federal government ($202.90/month), though high earners may pay an additional adjustment (IRMAA). Premium costs for drug plans, Medicare Advantage, or Supplement (Medigap) plans vary depending on the private carrier and benefits you select.

Can I keep putting money into my Health Savings Account (HSA)?

No. Once you enroll in any part of Medicare—even premium-free Part A—federal tax rules mandate that you stop making new tax-free contributions to your HSA. You can, however, continue spending any money already sitting in your account tax-free on qualified healthcare expenses.

What happens if I miss my signup deadline?

If you delay enrolling without having active, creditable insurance through a large employer, Medicare assesses permanent late-enrollment penalties:

  • Part B Penalty: Adds an extra 10% to your monthly Part B premium for every 12-month period you were eligible but un-enrolled. 
  • Part D Penalty: Adds a monthly fee (1% per month delayed) to your drug coverage for as long as you hold a policy.
Will I be able to keep seeing my current doctors?

If you choose Original Medicare (with or without a Medigap plan), you can see any provider in the country who accepts Medicare. If you choose a Medicare Advantage plan, you must verify that your primary care physician and specialists participate in that specific plan's HMO or PPO network.

Can I add my younger spouse or kids to my Medicare plan?

No. Medicare policies are strictly individual. There are no family, spousal, or dependent options. If you switch to Medicare and drop an employer plan that covers your younger spouse, they will need to secure their own coverage (such as through the Health Insurance Marketplace or COBRA) until they become eligible at age 65.

How do I sign-up if I am older then 65 and still working, but choose to take Medicare?

To enroll in Part B after age 65 Initial Enrollment Window without penalty(working or not), you must submit two forms to Social Security:

  1. Form CMS-40B: Your application for Medicare Part B.
  2. Form CMS-L564: Completed by your employer to prove you had continuous, creditable health coverage since turning 65.

Once Medicare approves you, they will send you a card that has your Medicare Identification Number and your effective dates for both A & B.

*PLEASE NOTE: We walk provide you with forms and walk you through entire process.

Credentials & Compliance

Written by: MediPlans NJ

Credentials: Licensed Independent Health & Medicare Insurance Advisors

Location: Cherry Hill, New Jersey

Editorial Integrity: This guide is published in compliance with CMS guidelines. MediPlans NJ provides independent, unbiased comparisons across Medicare Advantage, Medigap, and Part D plans to help consumers make confident decisions.

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