Working Past 65? Here’s What You Need to Know About Medicare & Employer Health Coverage

These days, 65 isn’t what it used to be.Many people are working well beyond their 65th birthday — whether for financial reasons, to stay busy, or simply because they love what they do.

But if you’re working past 65, there’s one thing you don’t want to ignore: Your Medicare options.

Medicare works a little differently when you’re still employed, and if you don’t know the rules, it’s surprisingly easy to make costly mistakes — penalties that can stick with you for life.

So let’s walk through it all, in plain English:

  • How Medicare works with employer health insurance
  • When you should (or shouldn’t) enroll
  • What happens with COBRA
  • How Special Enrollment Periods work
  • What proof of coverage you need to avoid penalties
  • And answers to the 10 most common questions I hear as a Medicare broker

Why This Matters More Than Ever

Over 25% of Americans age 65–74 are still working — and that number is growing every year.

Many employers offer health plans that seem better than Medicare — but things aren’t always as simple as they appear.

If you’re not careful, you could end up paying permanent penalties, face coverage gaps, or lose access to certain benefits when you do transition to Medicare.

The good news? When you understand the rules, you can make smart choices and avoid headaches down the road.

How Medicare Works With Employer Group Health Insurance

Here’s the basic rule of thumb:

If your employer has 20 or more employees:

  • You can delay enrolling in Medicare Part B (medical insurance) without penalty.
  • Your group health plan pays first (primary), Medicare pays second (secondary) — if you enroll in Medicare.
  • Many people choose to stay on their employer plan until they retire.

If your employer has fewer than 20 employees:

  • Medicare becomes your primary insurance once you’re eligible.
  • You should enroll in Medicare Part A and Part B to avoid paying out of pocket — your group plan may not cover costs Medicare would normally pay.

IIf your coverage is retiree coverage (not active employment):

  • Medicare is your primary coverage — you should enroll in Part A and Part B.

Do You Have to Enroll in Medicare at 65?

If you have active employer coverage through an employer with 20+ employees, you do not have to enroll in Medicare Part B at 65 — you can delay it without penalty.

But here’s where it gets tricky:

If you delay Part B when you should not have — or if you rely on coverage like COBRA or retiree insurance — you can face a 10% permanent penalty on your Part B premium for every 12 months you should have had it.

Important: Why You Shouldn’t Rely on COBRA

COBRA is not creditable coverage for delaying Medicare.
This is one of the biggest mistakes I see:

  • Many people think COBRA allows them to delay Medicare.
  • It doesn’t — and the clock starts ticking on your Part B late enrollment penalty the moment you stop active employment.

If you take COBRA and don’t enroll in Part B, you can be hit with both a penalty and a gap in coverage when COBRA runs out.

Real-life example:

One of my clients was offered COBRA after retiring at 67. They assumed they could wait to enroll in Medicare until COBRA ended. When they came to me, they’d already missed their enrollment window — and were facing a permanent penalty and had to wait months for coverage to begin.

Moral of the story: Don’t rely on COBRA as a Medicare substitute.

Special Enrollment Periods: Timing Is Everything

When you leave employer coverage, you qualify for a Special Enrollment Period (SEP) — which gives you a limited time to enroll in Medicare Part B and Part D without penalty.

Key points:

  • You have 8 months from the end of employer coverage to enroll in Part B.
  • You have 63 days from the end of employer coverage to enroll in Part D (prescription drug coverage).
  • If you miss this window, you’ll have to wait for the General Enrollment Period (Jan 1–Mar 31) — and face late enrollment penalties.

IMPORTANT: When you do enroll, you’ll need to show proof of prior creditable employer coverage to avoid penalties.
This means getting a letter from your employer or insurance carrier verifying that you had coverage through active employment.
No proof = penalties.

Medicare Enrollment Timing Tips

Here’s a smart timeline if you’re retiring soon:

  • Talk to HR at least 3–4 months before leaving your job.
    Ask for written proof of coverage (you’ll need it for Medicare).

  • Apply for Medicare Part B 2–3 months before your employer coverage ends.
    This helps ensure no coverage gap

  • Stop contributing to your HSA (if applicable) 6 months before enrolling in Medicare.
    Once you’re on any part of Medicare, you can’t contribute to an HSA.

What About HSAs?

If you’re still working and have a Health Savings Account:

  • You can contribute to your HSA only if you are not enrolled in Medicare Part A or Part B

  • Once you enroll in Medicare (even Part A), you must stop contributing to avoid tax penalties.

  • You can still spend HSA funds on qualified medical expenses after enrolling.

Top 10 Questions Medicare Consumers Ask About Working Past 65

  1. Do I need to enroll in Medicare at 65 if I’m still working?
    Not if your employer has 20+ employees and offers good coverage.

  2. What if my employer coverage is very good — should I delay Medicare?
    It depends. Some people enroll in Part A (usually free) and delay Part B if their group plan is excellent.

  3. What if my employer has fewer than 20 employees?
    You must enroll in Medicare — it will become primary.

  4. How does Medicare coordinate with my group plan?
    If your employer has 20+ employees: employer plan = primary, Medicare = secondary.

  5. What happens if I stay on COBRA and delay Medicare?
    You’ll face penalties and coverage gaps — always enroll in Medicare on time.

  6. What is the penalty for late enrollment?
    10% of your Part B premium for every 12-month period you delay.

  7. What is a Special Enrollment Period and how does it work?
    An 8-month window after your group coverage ends to sign up for Part B without penalty.

  8. When should I stop contributing to my HSA?
    At least 6 months before starting Medicare.

  9. How do I avoid coverage gaps when retiring mid-year?
    Apply for Medicare before your employer coverage ends to ensure seamless coverage

  10. Can my spouse stay on my employer plan if I switch to Medicare?
    Often yes — but confirm with your employer’s HR department.

Real-Life Story: Smooth Sailing With the Right Advice

A client of mine, Susan, planned to retire at 68. We worked together 4 months in advance to coordinate her Medicare enrollment. We requested proof of her employer coverage, timed her Part B application perfectly, and transitioned her to a great Medicare plan — with zero gaps in coverage and no penalties.

It pays to plan ahead — and to ask for expert guidance.

Final Thoughts: Get Personalized Help — Don’t Guess!

Here’s the bottom line:
There is no one-size-fits-all answer when working past 65. Every situation is unique, and the decisions you make today will affect your coverage — and your wallet — for years to come.

Want to avoid mistakes and penalties?
Want to ensure your transition from group insurance to Medicare is smooth and seamless?

That’s what I do every day. As an independent Medicare broker, I’ll help you navigate your options, compare plans, and handle the paperwork — so you can focus on enjoying life, not stressing about insurance.

Related Post

Does Medicare Pay For Cataract Surgery? Understanding Coverage Options and Costs

Cataracts are a common issue that can significantly impact your vision and daily activities. Medicare does provide coverage for cataract surgery when it is deemed medically necessary, ensuring you can regain clarity in your eyesight. Understanding what Medicare covers in relation to cataracts is crucial for making informed decisions about your eye health.

Navigating Medicare’s coverage can be complex, but it’s vital. With Medicare Part B typically covering the surgery itself and necessary intraocular lenses, you can focus on recovery rather than financial stress. For personalized assistance, The Modern Medicare Agency stands out as the best choice for your Medicare Insurance needs. Our licensed agents are real people available for one-on-one conversations, helping you find packages tailored to your requirements without unexpected fees.

Your vision health matters, and knowing how Medicare supports your needs is the first step in maintaining your quality of life. Engaging with The Modern Medicare Agency can provide clarity and confidence as you explore your options for cataract surgery coverage.

Medicare Coverage for Cataract Surgery
Medicare provides coverage for cataract surgery when it is deemed medically necessary. Understanding eligibility, the types of surgeries covered, and the required documentation is crucial for navigating your options.

Eligibility Requirements for Coverage
To qualify for Medicare coverage for cataract surgery, you must be enrolled in Original Medicare (Part A and Part B). Your ophthalmologist must diagnose you with cataracts that impair your vision, significantly affecting daily activities such as reading or driving.

Typically, Medicare covers the surgery when the cataract causes vision impairment; this is assessed based on specific criteria set by the Centers for Medicare & Medicaid Services. If you are covered by a Medicare Advantage plan, check with your plan provider for additional requirements, as benefits may vary.

Types of Cataract Surgeries Covered
Medicare generally covers various types of cataract surgeries, primarily focusing on procedures that are medically necessary. The most common type covered is phacoemulsification, which involves using ultrasonic waves to break up the cloudy lens for easier removal.

Laser-assisted cataract surgery is also covered if deemed medically necessary. Both types of surgery are outpatient procedures, meaning that you won’t need an overnight hospital stay. It’s essential that the surgeries are performed by a Medicare-enrolled supplier to ensure coverage.

Medical Necessity and Documentation
For coverage to be approved, you must provide documentation that supports the medical necessity of the surgery. This includes a detailed examination report from your ophthalmologist, outlining the extent of the cataracts and the resulting vision impairment.

This documentation is critical when submitting claims to Medicare. Your doctor may also need to provide a statement that confirms the need for surgery to restore vision functionality. Ensure your ophthalmologist is familiar with these requirements to facilitate a smoother claims process.

The Modern Medicare Agency can guide you through the specifics of Medicare plans. Our licensed agents provide personalized support to help identify the best coverage options for your needs without additional costs.

Costs and Out-of-Pocket Expenses
When considering cataract surgery, understanding the associated costs and out-of-pocket expenses is crucial. In this section, you will find detailed information about the breakdown of surgery costs, differences in pricing at various facilities, and the potential financial implications of Medicare and supplemental plans.

Breakdown of Surgery Costs
Cataract surgery costs can vary significantly based on several factors. Typically, the average cost for one eye ranges from $3,500 to $7,000. This price may cover pre-operative exams, the surgical procedure itself, and post-operative care. Medicare Part B primarily covers the standard costs associated with the surgery after you meet your deductible.

You may be responsible for a coinsurance payment of around 20% of the Medicare-approved amount after satisfying the deductible. It’s essential to verify what your specific plan covers and whether additional fees apply.

Hospital Outpatient vs Ambulatory Surgical Center Pricing
Costs can differ depending on whether the surgery is performed in a hospital outpatient department or an ambulatory surgical center. Ambulatory surgical centers often have lower costs compared to hospital outpatient facilities.

For instance, the average cost in an ambulatory surgical center may be around $3,500, while hospital outpatient settings might charge up to $5,000 or more. Always inquire about the exact location where your surgery will take place to avoid unexpected expenses.

Cost-Sharing and Coinsurance
Once you have met your Medicare Part B deductible, you will typically face cost-sharing through coinsurance. This usually requires you to pay about 20% of the Medicare-approved amount for the surgery.

It’s vital to note that the total amount you pay will depend on your chosen facility and any additional services you might need, such as advanced IOL lenses, which Medicare may not fully cover.

Role of Medigap and Medicare Supplement Plans
Medigap plans can be advantageous if you wish to minimize your out-of-pocket expenses for cataract surgery. These plans may cover costs not included in Medicare, such as coinsurance, and can significantly reduce your financial burden.

Choosing a Medicare supplement plan is crucial for comprehensive coverage, especially for expenses that Medicare does not fully cover. The Modern Medicare Agency can assist you in identifying plans that match your needs without incurring extra fees.

Consider discussing your options with a licensed agent from The Modern Medicare Agency, who can provide personalized assistance tailored to your situation. They enable you to navigate through Medicare packages efficiently, ensuring you select the best coverage without excess financial strain.

Intraocular and Advanced Lens Options
When undergoing cataract surgery, it’s essential to understand the various intraocular lens (IOL) options available. You’ll encounter standard and advanced lenses, each with distinct features and coverage under Medicare. Understanding these choices helps you make an informed decision based on your vision needs.

Standard Intraocular Lenses (IOLs)
Standard intraocular lenses are typically covered by Medicare. These monofocal lenses are designed to provide clear vision at one distance, whether that be near or far. After your cataract surgery, these lenses can help replace the cloudy lens that impaired your vision.

Medicare covers the cost of the surgeon’s fees and the procedure itself, as long as it is deemed medically necessary. You will pay 20% of the Medicare-approved amount after meeting the Part B deductible.

For those primarily needing distance vision correction, standard IOLs can be a practical and cost-effective choice.

Premium and Multifocal Lens Coverage
Premium lenses, including multifocal and advanced technology lenses, offer more flexibility in vision correction. These lenses can help you see clearly at multiple distances, which is particularly beneficial if you engage in activities requiring various focal points, such as reading and driving.

Medicare typically covers only the cost of standard IOLs. If you opt for premium lenses, you might incur additional out-of-pocket expenses. These can range significantly, often totaling several thousand dollars.

Understanding the various premium lens options allows you to weigh the benefits against the additional costs, ensuring you make a choice that suits your vision requirements.

Limitations on Advanced Technology Lenses
While advanced technology lenses like toric or multifocal options provide improved vision correction, they come with limitations under Medicare coverage. These lenses may address multiple vision issues, such as astigmatism or presbyopia, but they are considered enhancements.

If you choose these advanced options, be prepared for higher costs. Medicare generally does not cover the additional fees associated with these lenses. Therefore, evaluate your financial situation and vision needs carefully.

Working with a knowledgeable representative from The Modern Medicare Agency can help clarify your options and potential costs. Our licensed agents provide personalized support to ensure you find a Medicare plan that fits your needs.

Coverage for Glasses, Contacts, and Post-Surgery Care
Understanding the specifics of Medicare coverage for glasses and contacts after cataract surgery is essential. Additionally, knowing about prescription medications and eye drop coverage helps you better prepare for post-surgery care.

Eyeglasses and Contact Lenses After Surgery
Medicare Part B provides coverage for one pair of eyeglasses or one set of contact lenses following cataract surgery where an intraocular lens (IOL) is implanted. This benefit aims to support your vision correction needs after the procedure. Eyeglasses coverage typically includes standard frames, while contact lenses must be prescribed by a medical professional.

It’s crucial to order your corrective glasses or contact lenses in a timely manner to ensure they align with Medicare’s specific guidelines. Consult your eye care professional to coordinate purchases effectively and avoid any potential out-of-pocket costs.

Prescription Medications and Eye Drops
After cataract surgery, your physician may prescribe medications and eye drops to aid in recovery. While Medicare Part B covers certain post-surgery medication costs, you may need to consider Medicare Part D for broader prescription coverage.

Eye drops, particularly those used for inflammation or infection, are often covered if they are deemed medically necessary. Be sure to discuss your prescriptions with your healthcare provider and confirm which costs are covered under your plan.

Provider and Supplier Requirements
When obtaining eyeglasses or contact lenses through Medicare, ensure that you work with a Medicare-enrolled supplier. These providers meet the necessary standards to process your claims efficiently.

Additionally, confirm that your supply and accommodation needs align with Medicare requirements. This step will help guarantee timely coverage and reimbursement. Working with The Modern Medicare Agency can simplify this process. Our licensed agents support you through every step, providing personalized guidance without hidden fees. You deserve clear, straightforward assistance with your Medicare Insurance needs.

Choosing a Provider and Maximizing Medicare Benefits
Selecting the right provider and facility for cataract surgery is crucial to ensure you get the most out of your Medicare benefits. Understanding your options can lead to significant cost savings.

In-Network Providers and Facility Selection
Start by choosing an in-network provider to maximize your Medicare coverage. Look for ophthalmologists or eye doctors affiliated with your Medicare plan. They can perform cataract surgery at hospital outpatient centers or ambulatory surgical centers that accept Medicare.

Using an in-network facility can lower your out-of-pocket expenses significantly. Check with your Medicare Advantage plan to identify preferred providers. This can help you avoid additional costs and ensure a smoother process.

Ensure the provider you select is experienced in cataract surgeries. Ask about their track record and patient outcomes. This information can guide your decisions and may impact your recovery and satisfaction with the procedure.

Steps to Lower Out-of-Pocket Costs
To minimize your out-of-pocket costs, consider a few strategies. First, consult with The Modern Medicare Agency, where licensed agents can help you navigate your options. They can identify Medicare packages tailored to your needs without hidden fees.

Confirm that your surgical center is certified and part of your plan. Ask your provider about the cost-sharing required for surgery and any follow-up care that might also be covered.

Additionally, inquire about available vision care benefits after surgery. While Original Medicare covers post-operative eyeglasses or contacts, make sure you understand which options are available under your specific plan.

By carefully selecting your provider and facility, you can take full advantage of Medicare benefits while ensuring the best care for your cataracts.

Cataract Surgery and Eye Health Considerations
Cataracts can significantly affect your vision and overall eye health. Understanding their impact, the benefits of surgery, and the importance of regular eye exams is essential for maintaining healthy vision.

Impact of Cataracts on Vision
Cataracts occur when the lens of your eye becomes cloudy, leading to various symptoms. You may experience blurry vision, double vision, or difficulty seeing at night, which can obstruct daily activities such as reading or driving.

As cataracts progress, the vision impairment may become more severe, potentially leading to blindness if left untreated. Early detection is crucial, so pay attention to any changes in your eyesight and consult your eye care professional when necessary.

Benefits of Cataract Surgery for Preventing Blindness
Cataract surgery is often necessary to restore clear vision and prevent further complications. The procedure involves removing the cloudy lens and replacing it with a clear artificial lens.

This surgery can improve not only your vision but also your quality of life. Many patients report enhanced ability to perform daily tasks, reduced dependency on corrective eyewear, and an overall sense of autonomy.

Additionally, timely surgery can prevent progression to more severe vision issues, helping to avoid severe outcomes like blindness. It’s a proven and effective approach to managing cataracts.

Ongoing Eye Exams and Vision Care
Regular eye exams are essential for maintaining your ocular health, especially if you are at risk for cataracts or other eye conditions. These exams allow your eye doctor to monitor for changes and catch potential problems early.

During these appointments, your doctor will assess your vision and provide tailored recommendations for your eye care needs. Incorporating a comprehensive approach, including lifestyle changes, can improve your long-term eye health.

At The Modern Medicare Agency, our licensed agents can assist you in understanding your Medicare options for eye care. Personalized support ensures you find the best care without excessive costs. Schedule a consultation to discuss your vision care needs and ensure optimal eye health.

Frequently Asked Questions
Understanding Medicare coverage for cataract surgery involves knowing the specifics about lens implants, the extent of coverage for laser procedures, and other key details. Here are some common questions that may help clarify your concerns.

What type of lens implants are covered by Medicare during cataract surgery?
Medicare generally covers standard lens implants that are necessary for vision correction after cataract surgery. These include basic monofocal lenses, which typically provide clear vision at one distance. If you choose specialized lenses, such as multifocal or accommodating lenses, additional costs may apply.

Is cataract surgery for astigmatism covered by Medicare?
Yes, Medicare covers cataract surgery for patients with astigmatism, provided it is deemed medically necessary. The coverage includes the removal of the cataract and the insertion of a standard lens, but options for correcting astigmatism may require additional out-of-pocket expenses.

To what extent does Medicare cover the cost of laser cataract surgery?
Medicare does cover laser cataract surgery, as long as it is medically necessary. However, you may be responsible for a portion of the costs, such as deductibles and copayments. It’s essential to check your specific plan for details on any additional charges.

Are there specific cataract surgery procedures that Medicare does not cover?
Medicare may not cover certain elective procedures or specialized surgeries that extend beyond the standard cataract removal and lens implantation. Procedures that involve advanced techniques or additional features may incur extra costs.

Do lens implants following cataract surgery receive coverage under Medicare?
Yes, Medicare covers lens implants following cataract surgery, but only for standard monofocal lenses. If you opt for premium lenses or procedures that enhance vision capabilities, you may have to pay more out of pocket.

At what age is cataract surgery typically covered by Medicare?
Medicare does not have a specific age requirement for covering cataract surgery. Coverage is available if the surgery is judged necessary based on medical evaluations, regardless of the patient’s age.

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