Top 8 Medicare enrollment questions Clients Ask Me (And the Surprising Answers)

Real-life Medicare enrollment question example showing how misunderstanding timing can cost thousands

Did you know that 70% of Medicare beneficiaries have at least one major misunderstanding about their coverage? After helping thousands of clients navigate Medicare, I’ve noticed the same Medicare enrollment questions come up again and again, often with answers that surprise people.

Whether you’re new to Medicare or have been enrolled for years, there are crucial details about coverage, costs, and Medicare enrollment questions that many people miss. These misunderstandings can lead to thousands in unnecessary expenses or gaps in critical healthcare coverage.

In this article, I’ll share the top Medicare enrollment questions my clients ask about Medicare, along with the honest, expert answers you won’t always hear elsewhere. By the end, you’ll have clearer, more accurate information to make confident Medicare decisions.

 Group of older adults attending a Medicare workshop where a speaker is addressing Medicare enrollment questions

The Top 8 Medicare enrollment questions my clients ask me

Here are the top 8 Medicare enrollment questions my clients ask about Medicare, along with the honest, expert answers you won’t always hear elsewhere.

What’s the Difference Between Original Medicare and Medicare Advantage?

This is the #1 question I hear, and most people don’t realize:

  • Original Medicare (Parts A & B) Nationwide acceptance (any doctor who takes Medicare) No network restrictions Requires supplemental coverage (Medigap + Part D)
  • Medicare Advantage (Part C) Bundles Parts A, B, and usually D Often includes extra benefits (dental, vision) Has network restrictions like an HMO/PPO

Surprising Fact: 22% of Medicare Advantage enrollees try to switch back to Original Medicare within 3 years (KFF, 2023).

Supplemental Coverage Options: Medigap vs. Medicare Advantage

When Original Medicare (Parts A and B) doesn’t cover everything, many people look to supplemental coverage. Two popular options are Medigap plans and Medicare Advantage plans, but they work very differently.

  • Medigap (Medicare Supplement Insurance) Sold by private insurers to fill “gaps” in Original Medicare coverage, like deductibles, coinsurance, and copayments. Provides predictable out-of-pocket costs, often with nationwide coverage. Requires separate enrollment in a standalone Part D plan for prescription drugs. Best suited for people who want flexibility in choosing doctors and hospitals without network restrictions.
  • Medicare Advantage (Part C) An “all-in-one” plan that bundles Parts A, B, and usually D (prescription drugs). Often includes extra benefits like dental, vision, and fitness programs. Usually has network restrictions similar to HMOs or PPOs, which means you must use in-network providers for lowest costs. Can be more cost-effective for those who prefer integrated coverage and access to additional perks.

Which is better? It depends on your health needs, budget, and preference for provider choice. If you value broad provider access and predictable costs, Medigap might be ideal. If you prefer lower premiums with extra benefits and don’t mind network limits, Medicare Advantage could work well.

When Exactly Should I Enroll in Medicare?

The enrollment rules trip up more people than any other Medicare topic, and this raises many Medicare enrollment questions:

  • Initial Enrollment Period: 7-month window around your 65th birthday month
  • General Enrollment Period: Jan 1-Mar 31 each year (with penalties)
  • Special Enrollment Periods: For those with employer coverage

Critical Detail: If you miss your Initial Enrollment Period, you may face permanent late penalties on your premiums, a common concern among those with pressing Medicare enrollment questions.

Who qualifies for premium-free Part A? Eligibility and Cost Factors

Who qualifies for premium-free Part A? Most people qualify if they or their spouse have paid Medicare taxes for at least 10 years. If not, you can buy Part A by paying a monthly premium.

Part B and Part D premiums vary by income:

  • Higher-income beneficiaries pay higher premiums for Part B and Part D.
  • For 2024, the standard Part B premium is $174.70/month, but it increases for those with modified adjusted gross incomes above $97,000 (individual) or $194,000 (joint).
  • Part D premiums and penalties are also income-based.

Understanding these factors early can help answer some of your Medicare enrollment questions and plan your Medicare enrollment and budget more effectively.

Smiling senior couple holding a Medicare info packet after getting answers to their Medicare enrollment questions

How Can I Avoid Medicare Penalties?

Follow these 3 key steps to avoid common penalties associated with Medicare enrollment questions:

  • Mark your 65th birthday month on your calendar
  • Confirm if you need to enroll (even if still working)
  • Get Part D coverage even if you don’t take prescriptions

Surprising Fact: The Part D penalty is 1% of the national base premium for every month you delay enrollment without creditable coverage.

How can I Understand Medicare Part D: Prescription Drug Coverage

Medicare Part D provides prescription drug coverage through private plans approved by Medicare. Here’s what you need to know, information that often surfaces in Medicare enrollment questions:

  • Each plan has a formulary, a list of covered drugs that can vary widely between plans. Always check if your medications are included.
  • Plans have different tiers, affecting your copayments or coinsurance for each drug.
  • Be aware of the “donut hole” or coverage gap: after you and your plan spend a certain amount on covered drugs, you may pay higher out-of-pocket costs until you reach catastrophic coverage. However, recent changes have reduced the financial impact of this gap.
  • Missing Part D enrollment without “creditable” drug coverage (like through an employer) may result in lifelong penalties, increasing your premiums.

To avoid surprises, review Part D plans annually and choose one that best fits your medication needs, this is a top concern in many Medicare enrollment questions.

What Does Medicare NOT Cover?

Most people are shocked to learn Medicare doesn’t cover:

  • Routine dental care (cleanings, fillings, dentures)
  • Eye exams and glasses (except after cataract surgery)
  • Hearing aids and exams
  • Long-term care (nursing homes, assisted living)

Solution: Consider supplemental policies for these common needs, something many ask about in their Medicare enrollment questions.

What are the Common Medicare Mistakes & How to Avoid Them

  • Mistake #1: Assuming Medicare is Free
    While Part A is often premium-free, you’ll still pay:
    • Part B premiums ($174.70/month in 2024)
    • Deductibles and coinsurance
    • Prescription drug costs
      How to Avoid: Budget $200-$400/month for Medicare expenses, which is an important note when addressing Medicare enrollment questions.
  • Mistake #2: Not Reviewing Plan Changes Annually
    Reality: Medicare Advantage and Part D plans change every year, often increasing costs or reducing benefits.
    How to Avoid: Always review your Annual Notice of Change (ANOC) each September.
  • Mistake #3: Waiting Until Retirement to Learn About Medicare
    Reality: Some Medicare decisions (like Medigap enrollment) have strict time windows that are easy to miss.
    How to Avoid: Start researching Medicare at least 6 months before turning 65 to avoid last-minute Medicare enrollment questions.
Elderly woman on a phone call with a Medicare advisor, asking Medicare enrollment questions from home

Common Medicare Myths Debunked

1. Myth: Medicare is free.

This is one of the most widespread misunderstandings and it comes up constantly in Medicare enrollment questions. While Part A is typically premium-free for those who’ve paid into Medicare through payroll taxes for at least 10 years, that’s just one part of the puzzle. You’ll still have to pay a monthly premium for Part B, which is $174.70/month in 2024 for most people, along with deductibles, copayments, and coinsurance.

If you add Part D for prescription drugs, expect additional monthly premiums and potential out-of-pocket costs for medications. Those considering Medicare Advantage plans may have lower or $0 premiums, but costs often appear through copays, network restrictions, and uncovered services.

2. Myth: Medicare covers all healthcare costs.

A major surprise for many is just how much Original Medicare doesn’t cover, including some of the most common healthcare needs. Medicare excludes routine dental care, eye exams and glasses, hearing aids, and long-term care services such as custodial care in nursing homes or assisted living.

These services must be paid out of pocket or covered through other insurance, such as dental/vision add-ons with Medicare Advantage, or separate standalone policies. This lack of comprehensive coverage frequently leads to follow-up Medicare enrollment questions about supplemental plans like Medigap.

3. Myth: You can change Medicare plans anytime.

Unlike standard health insurance through the ACA marketplace or employer coverage, Medicare changes are restricted to very specific timeframes. The Annual Enrollment Period (AEP) from October 15 to December 7 allows you to switch between Medicare Advantage and Original Medicare or change drug plans.

Medicare Advantage Open Enrollment (Jan 1–Mar 31) lets those already in an Advantage plan make a one-time switch. Outside of these windows, you typically need to qualify for a Special Enrollment Period (SEP) due to life changes like moving or losing coverage. Many people ask Medicare enrollment questions too late, after their opportunity to switch has passed.

4. Myth: If I’m working past 65, I don’t need Medicare.

This myth can lead to costly penalties and coverage gaps. If you’re working and have employer health coverage, whether you need to enroll in Medicare depends on the size of your employer and how your plan coordinates with Medicare. For companies with fewer than 20 employees, Medicare is typically primary, and delaying enrollment can trigger late penalties for both Part B and Part D. For larger employers, you may be able to delay Parts B and D without penalties, but you must document creditable coverage.

These nuanced situations are a top source of confusion and of Medicare enrollment questions from clients nearing age 65.

Medicare Case Study: John’s $5,000 Mistake

John, 67, assumed his retiree health plan was “better than Medicare” and delayed enrollment. When he finally signed up:

  • He owed 12 months of back premiums
  • Faced permanent late penalties adding $35/month to his Part B
  • Couldn’t get a Medigap plan due to health conditions

Total extra costs: Over $5,000 in the first 5 years. This kind of costly outcome is what many hope to avoid when they seek answers to their Medicare enrollment questions.

More Surprising Medicare Answers

Can I keep my doctor with Medicare?

Yes with Original Medicare (if they accept Medicare)
Maybe with Medicare Advantage (must be in-network)

Does Medicare cover me overseas?

Generally no, except in rare cases near U.S. borders

Can I change plans anytime?

Only during specific enrollment periods (except special circumstances)
These are among the most common Medicare enrollment questions we hear.

Conclusion

Medicare is far more complex than most people realize, and small misunderstandings can lead to costly mistakes. Now that you know the answers to these common Medicare enrollment questions, you’re better prepared to navigate Medicare confidently.

Don’t do it alone when it comes to understanding Medicare. Our experienced brokers are ready to help you. Call us today at 734-740-3997 or visit our Contact Us page for a free, no-obligation consultation.

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