Enrolling in Medicare at the appropriate time—or failing to—can have lifelong consequences. So it’s really important that it be done right. (For manual enrollment of Medicare, please see our step-by-step guide on “How to enroll in Medicare.”)

Do You Need to Enroll in Medicare at 65?

Reaching the age of 65 often marks a significant milestone, especially when it comes to healthcare decisions. If you’re still actively employed at this stage in life, there are some unique things to think about when it comes to Medicare.

Whether you need to enroll in Medicare when you turn 65 depends on several factors, including your employment situation and existing health coverage. Here’s a breakdown of different scenarios.

1. Employed With Over 20 Employees and Job-Based Health Insurance

If you’re working for an employer with more than 20 employees and have health insurance through your job, you have the option to wait to sign up for Part B (Medical Insurance) until you or your spouse stop working or lose your insurance. Waiting to enroll, in this case, won’t result in a late enrollment penalty. If you’re eligible for premium-free Part A (Hospital Insurance), you can choose to enroll at 65 or later. Start a quote today to find out if you qualify!

In this situation, job-based insurance pays first, and Medicare will pay second.

2. Employed With Fewer Than 20 Employees and Job-Based Health Insurance

If your employer has fewer than 20 employees and provides your health insurance, you can also wait until you or your spouse stop working or lose coverage before enrolling in Part B without a late enrollment penalty. However, you should check with your employer about whether you need to sign up for both Part A and Part B. Failure to do so might lead to gaps in coverage. If you get Medicare and keep your job-based insurance, Medicare pays first, and job-based insurance will pay second.

3. Employed with Non-Job Health Insurance (e.g., Medicaid or Marketplace)

If you or your spouse are still working, but your health insurance is not from your job, you will most likely need to enroll in both Parts Aad B of Medicare. To learn what Medicare rules apply to your situation, start a quote today.

4. Self-employed or With Insurance Not Available to Everyone at the Company

Those who are self-employed or have health insurance that’s not available to all employees at the company should ask their insurance provider if the IRS defines their coverage as an employer group health plan. If they don’t, signing up for Medicare at 65 is crucial to avoid paying monthly Part B late enrollment penalties. If you have retiree coverage from a prior job, you will need to enroll in Part A and Part B.

5. COBRA Coverage in Place

If you have COBRA coverage and haven’t enrolled in Medicare yet, it’s essential to sign up when you turn 65 to prevent coverage gaps and monthly Part B late enrollment penalties. COBRA coverage will end once you enroll in Medicare. Don’t wait until COBRA ends to sign up for Part B, as COBRA doesn’t extend your Medicare enrollment window.

6. COBRA Coverage After Medicare Enrollment

COBRA typically pays for healthcare costs after Medicare, except in cases of End-Stage Renal Disease. Review the specifics of COBRA and Medicare coordination to understand how it impacts your coverage.

7. Employer-Stipended Private Health Insurance

If you or your spouse receive a stipend from your employer to purchase private health insurance and are still working, you will need to enroll in both Part A and Part B at age 65.

8. Employed Without Any Health Insurance

For those who work past 65 without health insurance, you will need to enroll in both Part A (Hospital Insurance) and Part B (Medical Insurance) as soon as you’re eligible, typically at age 65. Waiting to enroll carries risks (in the form of penalties owed). If you aren’t sure you can afford insurance, there are ways to get help with your healthcare costs.

Signing Up for Medicare

Many people find Medicare confusing, but it doesn’t have to be. If you’re approaching the age of 65, it’s important to know the Medicare enrollment process and available coverage options before you sign up.

1. Automatic Enrollment for Social Security or Railroad Retirement Benefits Recipients

If you’re already receiving benefits from Social Security or the Railroad Retirement Board, you’ll be automatically enrolled in Medicare. There’s no need for any action on your part.

2. Manual Enrollment for Those Not Receiving Benefits

If you’re not currently receiving Social Security or Railroad Retirement benefits, you will need to manually sign up for Medicare. To find out how to do that, see our step-by-step guide on How to enroll in Medicare.”

3. Preparing for Retirement

If retirement is on the horizon for you within the next year, you’ll need to get the ball rolling by doing some research ahead of time. This will protect you from missing the brief enrollment window and help you avoid penalties.

4. Health Savings Account

If you have a Health Savings Account (HSA), you should cease contributions from both you and your employer six months before retiring or applying for Social Security or Railroad Retirement benefits. This proactive step helps avoid tax penalties from ongoing HSA contributions.

Exploring Coverage Options

Once you’ve enrolled in both Part A (Hospital Insurance) and Part B (Medical Insurance), you’ll have the flexibility to choose how you want to receive your Medicare coverage. Before making this decision, it’s vital to thoroughly understand your coverage options.

Timing for Additional Coverage

The timing to get additional coverage depends on the type of coverage you want.

Medicare Advantage Plan

You have a window of two months after your job-based insurance ends to join a Medicare Advantage Plan. If you want your plan’s coverage to begin immediately after your job-based insurance ends, it’s best to sign up for Medicare and enroll in a plan before your job-based coverage ends.

Medicare Drug Plan

Similar to the Medicare Advantage Plan, you have two months after your job-based insurance ends to join a Medicare drug plan. For a seamless transition, sign up for Medicare and select a plan before your job-based coverage ends.

Medicare Supplement Insurance (Medigap) Policy

If you’re 65 or older, you have a six-month window to purchase a Medigap policy after you get Part A and Part B. Learn more about Medigap options to make an informed decision.

Caution with Retiree Coverage

If your employer offers retiree coverage while you have Medicare, such as a supplemental plan, drug coverage, or Medicare Advantage Plan, you should ask whether you or your family members will lose coverage by joining a plan the employer doesn’t offer.

Maintaining Creditable Drug Coverage

If you have other creditable drug coverage, you can wait to enroll in a Medicare drug plan or a Medicare Advantage Plan with drug coverage.

  • To find out if your current drug plan qualifies as creditable coverage, ask your plan – they are obligated to tell you. They’ll also send the information about it annually.
  • Keep this information for future reference; you may need it when joining a Medicare drug plan. (You won’t need to send the info to Medicare though.)

Going more than 63 days without creditable drug coverage could result in the Part D late enrollment penalty.

Got Questions About Working with Medicare? We’ve Got Answers!

Navigating Medicare and keeping track of all the regulations can be exhausting, and if you’re working over the age of 65, you hardly have time to think about it. Thankfully, that’s why we’re here: we have been explaining insurance options to hard-working people like you for over 30 years! At Susan Polk Insurance, we’re always available and delighted to help. Start a quote today and let us take the mystery out of Medicare for you.

Don’t go a day without health insurance.

Since 1988, we’ve helped tens of thousands of people get the most out of their health insurance dollars, in SLO County and across California. Get a quote today and let us help you get the coverage you need at a price you can afford.