How do I sign up for Medicare?

Medicare enrollment depends on your situation. If you're already receiving Social Security benefits, you'll be automatically enrolled in Medicare Parts A and B at age 65. If you're not receiving Social Security, you'll need to sign up during your Initial Enrollment Period, which begins 3 months before your 65th birthday month and ends 3 months after.

What are the four parts of Medicare?

Medicare has four parts: Part A (Hospital Insurance) covers inpatient hospital stays, skilled nursing, and hospice care. Part B (Medical Insurance) covers doctor visits, outpatient care, and preventive services. Part C (Medicare Advantage) is an alternative to Original Medicare offered by private insurance companies. Part D covers prescription drugs.

Are there penalties and fees to watch for?

Yes, Medicare has late enrollment penalties if you don't sign up when first eligible. The Part B penalty is 10% of the premium for each 12-month period you could have had Part B but didn't sign up. Part D also has a penalty that's added to your premium permanently. Additionally, high-income earners may pay IRMAA (Income-Related Monthly Adjustment Amount) surcharges.

I'm still working. Do I need to sign up for Medicare?

If you're still working at 65 with creditable employer coverage (from an employer with 20+ employees), you can typically delay Medicare enrollment without penalty. However, if your employer has fewer than 20 employees, Medicare becomes primary and you should enroll at 65. Always verify your coverage is creditable to avoid future penalties.

Should I choose a licensed insurance broker or licensed insurance agent?

A licensed insurance broker represents you, the consumer, and can shop multiple insurance companies to find the best plan for your needs. They work with many carriers and are paid the same regardless of which plan you choose. This provides unbiased guidance and more options compared to a captive agent who represents only one insurance company.

How do I sign up for Medicare Advantage or Medigap?

To enroll in Medicare Advantage or Medigap, you must first be enrolled in Medicare Parts A and B. For Medicare Advantage, you can enroll during Annual Enrollment Period (October 15 - December 7) or during a Special Enrollment Period. For Medigap, the best time is during your 6-month Medigap Open Enrollment Period starting when you turn 65 and have Part B.

Medicare Supplement or Medicare Advantage?

Medicare Supplement (Medigap) works with Original Medicare and covers gaps like copays and deductibles, allowing you to see any doctor that accepts Medicare. Medicare Advantage is an all-in-one alternative to Original Medicare, often including prescription drug coverage and extra benefits, but typically requires using network providers. The choice depends on your healthcare needs, budget, and preference for provider flexibility.

What are the important dates and deadlines?

Key Medicare dates include: Initial Enrollment Period (3 months before through 3 months after your 65th birthday month), Annual Enrollment Period (October 15 - December 7 for plan changes), Medicare Advantage Open Enrollment (January 1 - March 31), and various Special Enrollment Periods triggered by qualifying life events. Missing these deadlines can result in coverage gaps and penalties.

I don't like my current plan. Can I change it?

Yes, you can change your Medicare plan during specific enrollment periods. Annual Enrollment Period (October 15 - December 7) allows you to switch between Original Medicare and Medicare Advantage, or change plans. Medicare Advantage Open Enrollment (January 1 - March 31) lets you switch Medicare Advantage plans or return to Original Medicare. Special Enrollment Periods may also apply based on qualifying events.

You cannot contribute to a Health Savings Account (HSA) once you enroll in any part of Medicare. You should stop HSA contributions 6 months before enrolling in Medicare due to retroactive enrollment rules. However, you can still use existing HSA funds tax-free for qualified medical expenses, including Medicare premiums, deductibles, and copays.

Medicare Advantage HMO vs. PPO: Which Is Right for You?

HMO (Health Maintenance Organization) plans typically offer lower premiums and require you to use network providers and get referrals for specialists. PPO (Preferred Provider Organization) plans offer more flexibility to see out-of-network providers without referrals, but usually cost more. Choose HMO for lower costs with a coordinated care approach, or PPO for provider flexibility and out-of-network coverage.

Senior still working at 65 reviewing Medicare enrollment options

Still Working at 65? Here's What You Need to Know About Medicare

Turning 65 doesn’t automatically mean you need to enroll in Medicare — especially if you’re still employed and have health coverage. Understanding your options can help you avoid unnecessary costs and coverage gaps.

Working at 65: Do You Have to Enroll in Medicare?

If you are still working and have employer-provided health insurance, you might be able to delay enrolling in Medicare Part B (and avoid paying the Part B premium) without penalty.

The rules depend on:

Employer Size:
- 20 or more employees: You can usually delay enrolling without penalties.
- Fewer than 20 employees: Medicare becomes your primary insurance, and you should enroll when first eligible.
Type of Coverage: COBRA, retiree coverage, and marketplace plans are not considered “active employer coverage” — you generally must enroll in Medicare to avoid penalties.

👉 Have an HSA? If so, it’s crucial you learn about the rules involving Medicare and HSA’s here!

Should I Still Enroll in Medicare Part A?

Yes — most people should enroll in Medicare Part A (hospital insurance) at 65, even if they’re still working.

Part A is usually premium-free if you or your spouse paid Medicare taxes for at least 10 years.
Having Part A can help cover hospital stays and some skilled nursing care.

👉 Need a refresher on Part A? Learn about the four Medicare Parts and what they cover here!

If you plan to retire later:

You qualify for a Special Enrollment Period (SEP) to sign up for Medicare without penalties.
SEP typically gives you 8 months after employment or group health coverage ends to enroll.

Penalties for Late Enrollment

If you don’t sign up on time when required, you could face:

Part B late enrollment penalty: A 10% increase in your premium for each full 12-month period you delay.
Part D late enrollment penalty: If you go without creditable drug coverage for 63+ days.

Avoiding these penalties starts with knowing whether you need to enroll while working.

Key Takeaways

If your employer has 20+ employees, you can delay Part B without penalty.
If your employer has fewer than 20 employees, you should enroll when first eligible.
Enroll in Part A at 65, unless you’re contributing to an HSA (Health Savings Account).

👉 If you see that you need to enroll, knowing the difference between seeking help from a licensed insurance broker or a licensed insurance agent can make a big difference. Learn more here!

Medicare While Still Working

Still Working at 65? Here's What You Need to Know About Medicare

Working at 65: Do You Have to Enroll in Medicare?

Should I Still Enroll in Medicare Part A?

Penalties for Late Enrollment

Key Takeaways

Need Help Deciding?

Talk to a knowledgeable licensed insurance agent. Understanding when and how to enroll can assist on maximizing your budget.