5 Costly Medicare Mistakes to Avoid in 2026

Medicare offers valuable coverage and peace of mind, but with so many parts, enrollment options, and deadlines, it’s easy to see how some details may get mixed up. With open enrollment for 2026 approaching, now is the perfect time to get familiar with your options and deadlines. Even those who feel prepared for open enrollment can find themselves with questions as they try to choose the right plan and ensure everything is in order.

This guide will walk you through five of the most common and expensive Medicare mistakes to watch for, sharing straightforward tips for sidestepping them with confidence. With a little preparation and the right information, you can secure the coverage you need and make the most of everything Medicare has to offer as you move toward a healthy and rewarding retirement.

Mistake 1: Missing Your Initial Enrollment Period

One of the most significant and costly errors is failing to sign up for Medicare during your Initial Enrollment Period (IEP). Your IEP is a specific seven-month window around your 65th birthday when you first become eligible for Medicare. It begins three months before the month you turn 65, includes the month of your birthday, and ends three months after.

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Mistake 2: Assuming Medicare Covers Everything

A common misconception is that once you're enrolled in Original Medicare (Part A and Part B), all your healthcare expenses are covered. Unfortunately, this is not the case. Original Medicare has significant gaps that can leave you with substantial out-of-pocket costs.

For example, Original Medicare typically doesn't cover:

  • Prescription drug & RX coverage
  • Routine dental care, including cleanings, fillings, or dentures
  • Eye exams for prescription glasses or contact lenses
  • Hearing aids and the exams for fitting them
  • Long-term care or custodial care

To fill these gaps, you have a couple of options. You can purchase a Medicare Supplement Insurance (Medigap) policy, which helps pay for some of the remaining healthcare costs like copayments, coinsurance, and deductibles. Another option is a Medicare Advantage (Part C) plan, which we will discuss next. Understanding these gaps is the first step toward building a comprehensive healthcare safety net

Mistake 3: Choosing the Wrong Medicare Plan

Selecting the right plan is crucial, and the choice between Original Medicare with a Medigap policy and a Medicare Advantage (Part C) plan is a major decision point. There's no one-size-fits-all answer; the best option depends entirely on your individual health needs, budget, and lifestyle.

Medicare Advantage vs. Medicare Supplement

Medicare Advantage plans are offered by private insurance companies approved by Medicare. They bundle Part A, Part B, and usually Part D (prescription drugs) into one plan. Many also offer extra benefits not covered by Original Medicare, like dental, vision, and hearing. However, they typically require you to use a network of specific doctors and hospitals.

On the other hand, Original Medicare with a Medigap policy offers more flexibility. You can see any doctor or visit any hospital in the U.S. that accepts Medicare. The Medigap policy helps cover the out-of-pocket costs of Original Medicare. This combination often comes with higher monthly premiums but can result in little to no out-of-pocket expenses when you need care.

To make the right choice, consider your doctor network, typical medical expenses, and how much risk you are willing to take on for out-of-pocket costs.

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Mistake 4: Ignoring Prescription Drug Coverage (Part D)

Prescription medications can be one of the most significant ongoing health expenses in retirement. That's why ignoring Medicare Part D is a mistake you can't afford to make. Part D provides coverage for prescription drugs and is available as a standalone plan to complement Original Medicare or as part of a Medicare Advantage plan.

Even if you don't currently take any prescription medications, it's wise to enroll in a Part D plan during your IEP. If you delay enrollment and don't have other creditable prescription drug coverage, you will likely face a permanent late enrollment penalty added to your monthly premium once you do sign up.

When choosing a plan, it's not just about how much Medicare Part D costs per month. You need to check the plan’s formulary (the list of covered drugs) to ensure your specific medications are included and to understand the copayments and coinsurance.

Mistake 5: Failing to Review Your Coverage Annually

Your healthcare needs can change from one year to the next. A plan that was perfect for you this year might not be the best fit next year. That's why failing to review your coverage annually is one of the most common costly Medicare mistakes.

Every year, from October 15 to December 7, Medicare holds its Open Enrollment Period. During this time, you can make changes to your coverage. You can switch from Original Medicare to a Medicare Advantage plan (or vice versa), change your Medicare Advantage plan, or switch your Part D prescription drug plan.

Insurers can also make Medicare changes each year. They might alter their provider networks, change the list of covered drugs, or adjust premiums and deductibles. Reviewing your plan annually ensures your coverage continues to meet your health and financial needs.

Find the Right Medicare Plan for You

Navigating Medicare doesn't have to be a solo journey fraught with potential errors. By understanding these five common mistakes—missing enrollment deadlines, underestimating coverage gaps, choosing the wrong plan, ignoring drug coverage, and failing to review your plan annually—you can take control of your healthcare future.

Being proactive is the key to securing peace of mind. If you need Medicare enrollment assistance or want to compare your options without sales pressure, we're here to help. At The Pocket Protector, our advisors offer independent, unbiased guidance to find the best fit for you.

Use our online Medicare enrollment tool to review your plan options today and ensure your coverage is ready for 2026.

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