5 Costly Medicare Mistakes to Avoid at 65

Updated on March 11, 2026
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Howard Yeh

Written by Howard Yeh

We aim to help you make informed healthcare decisions. While this post may contain links to lead generation forms, this won’t influence our writing. We follow strict editorial standards to give you the most accurate and unbiased information.

Turning 65 is a milestone. For many Americans, it’s also when health insurance shifts from employer coverage or the individual market to Medicare.

Making the switch to Medicare might seem straightforward. The reality is more complicated.

Medicare isn’t automatic in every situation. It’s also not free, and it’s definitely not simple.

Every year, thousands of Americans make avoidable and often costly mistakes when choosing coverage at 65. Some pay lifetime penalties for these mistakes.

If you’re approaching Medicare eligibility, here are five of the most common mistakes and how to avoid them.

Mistake #1: Assuming Medicare is Automatic for Everyone

Many Americans believe they’ll automatically be enrolled in Medicare when they turn 65.

That’s only partially true.

If you’re already receiving Social Security benefits, you’ll typically be automatically enrolled in Medicare Part A and Part B.

But if you’re not already collecting Social Security, you usually need to actively sign up.

This is where your Initial Enrollment Period becomes important. The Initial Enrollment Period is a seven-month window that begins three months before your 65th birthday, includes your birth month, and ends three months after.

If you miss your Initial Enrollment Period, you could pay permanent late enrollment penalties, especially for Part B and Part D.

How to Avoid this Mistake: Don’t assume enrollment is automatic. Confirm your status well before your 65th birthday. Then, mark your enrollment window on your calendar.

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Mistake #2: Delaying Medicare Without Understanding the Rules

Plenty of people continue working past 65. That’s not a problem, but misunderstanding how employer coverage works with Medicare can be.

If you (or your spouse) have employer coverage from a company with 20 or more employees, you may be able to delay Medicare Part B without penalty. But if the employer has fewer than 20 employees, Medicare typically becomes your primary coverage at 65, and delaying enrollment could lead to penalties.

Worse, some people assume COBRA coverage counts as employer coverage for Medicare delay purposes. It doesn’t.

The Part B penalty adds 10% to your premium for every 12-month period you were eligible but didn’t enroll. Unfortunately, that penalty lasts for life.

How to Avoid this Mistake: Before delaying any part of Medicare, confirm whether your employer coverage qualifies you to postpone enrollment without penalty.

Mistake #3: Choosing Medicare Advantage Without Reviewing Provider Networks

Medicare Advantage plans might dazzle you with low or even $0 monthly premiums.

However, premiums are just part of the story.

Medicare Advantage plans operate with provider networks. That means your preferred doctors, specialists, or hospitals may not be in-network.

This problem becomes worse if you travel frequently or split time between states, which is when network limitations can create more coverage headaches.

Unlike Original Medicare, which allows you to see nearly any provider nationwide who accepts Medicare, Advantage plans may restrict you to local networks except in emergencies.

How to Avoid this Mistake:

Before enrolling in a Medicare Advantage plan, answer questions like:

  • Are your doctors in-network?
  • Are your prescriptions covered?
  • What are the copays for specialists?
  • What is the out-of-pocket maximum?

Cheap or $0 premiums may look great. Read the fine print, however, to ensure you know exactly what you’re paying for (and what you’re giving up).

Mistake #4: Ignoring Prescription Drug Coverage

Like it or not, prescription drugs could be a significant part of your monthly budget as you age.

Even if you don’t take medications now, skipping prescription drug coverage (Medicare Part D) can be risky.

First, there’s a late enrollment penalty if you go without creditable drug coverage for 63 consecutive days or more after becoming eligible.

Second, health needs change: you might skip drug coverage at 65 only to face unexpected prescriptions later. Then, you discover you must wait until the next enrollment period to sign up.

How to Avoid this Mistake: Even with Medicare Advantage plans that include drug coverage, it’s important to review the plan’s formulary, which is the list of covered medications. Different plans cover different drugs on different tiers.

Evaluate drug coverage carefully, even if you take zero medications today and are perfectly healthy. You’ll be protected from penalties and future surprises.

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Mistake #5: Not Comparing Total Costs

One of the biggest misunderstandings about Medicare is cost.

Original Medicare includes:

  • Part A (Hospital coverage)
  • Part B (Medical coverage)

But it does not cap out-of-pocket costs. There’s no annual maximum under Original Medicare alone.

That’s why many people buy a Medicare Supplement (Medigap) policy to help cover deductibles, copays, and coinsurance.

Others choose Medicare Advantage, which does have an annual out-of-pocket maximum.

How to Avoid this Mistake: This is another situation where comparing potential total spending is more important than comparing monthly premiums alone:

  • An Advantage plan may have low premiums but higher copays and a higher out-of-pocket maximum
  • A Medicare Supplement plan may have a higher monthly premium but lower unexpected costs if you need frequent care

There’s no perfect answer. The “best” option depends on your health, travel habits, risk tolerance, and budget.

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Plan Ahead for Medicare at 65

Typically, mistakes with Medicare coverage and enrollment are due to things such as missing deadlines, focusing only on premiums, or not understanding how different parts of Medicare work together

Fortunately, you can avoid all of these mistakes with planning. As you approach 65, start planning at least three months before your birthday. Review your current coverage, confirm your enrollment window, compare plans carefully, and think about your long-term needs.

And if Medicare decisions ever feel overwhelming, visit MedicareGuide.com. We’re here to help.

Howard Yeh
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Howard Yeh


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