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7 Medicare Mistakes You May Be Making

Wealth | Updated: July 31, 2026
Nicole Pyles
Author
Based in Portland, Oregon, Nicole Pyles is an experienced freelance writer who writes about home and kitchen, health and wellness, and more. She's written for a variety of outlets, including Better Homes and Gardens, Tom's Guide, Better Report, and more.
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Better Report

More than 70 million Americans are on Medicare. Whether you’re 65 or older or have an eligible disability, Medicare can be a necessary lifeline that helps reduce the costs of medical care, prescriptions, and more. But the amount of information and the necessary steps involved in signing up or navigating a potential change in your plan can be overwhelming. We talked with Danielle Roberts, co-founder and Medicare insurance expert at Boomer Benefits, about the mistakes you could be making when it comes to Medicare — and how to avoid them. 

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Treating Medicare as a One-Size-Fits-All Benefit

Medicare isn’t the same for everyone. “Each person has their own eligibility, their own premiums, and their own enrollment timeline,” Roberts says. “Even within the same household, one spouse may be enrolled in Medicare while the other is not or may have completely different coverage rules.”

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Regardless of whether you and your spouse are enrolling at the same time, or your friend recommends a certain type of coverage, it’s important to make Medicare decisions based on what’s right for you as an individual. “Get started on your Medicare research several months in advance of your Medicare eligibility,” Roberts recommends. “Medicare decisions affect coverage, costs, and, in some cases, tax planning, so the timing matters.”

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Not Anticipating or Planning for Gaps in Medicare Coverage

Medicare, including Part A (hospital insurance) and Part B (medical insurance), isn’t comprehensive. “Part A and Part B still include deductibles, copayments, and coinsurance,” Roberts says. “For example, Part B generally covers 80% of approved outpatient services, leaving the remaining 20% as the beneficiary’s responsibility.”

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Whether you’re considering Medicare or planning to switch to another Medicare plan, focus on the services you’ll use. For example, most Medicare plans don’t include coverage of vision, hearing, and long-term care, according to Roberts. In that case, you may want to opt for one of the Medicare Advantage plans (Part C) that do include these services. Make sure to review them carefully to ensure they include your preferred doctors.

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Contributing to HSA Accounts

If you’ve enrolled in Medicare Parts A and B or a Medicare Advantage plan, you can no longer contribute to a Health Savings Account (HSA). Roberts says she often sees confusion about HSAs and Medicare. “Many people continue contributing to an HSA … without realizing the rules change at enrollment. Once Medicare begins, HSA contributions are no longer allowed. Continuing contributions can create unnecessary tax issues that are entirely avoidable with proper timing.”

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If you’re 65 or older, still working, and want to continue contributing to your HSA, you can delay enrolling in Medicare. Be aware, however, that there can be penalties for delaying enrollment, and if you delay, your  HSA contributions will need to stop six months before you ultimately apply for Medicare, Roberts says.

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But if you’re enrolling in Medicare at 65, according to Roberts, “you can keep contributing to your HSA all the way up until the day before your 65th birthday month.” The good news is, no matter when you join, you can still use your existing HSA funds for expenses such as copays and deductibles. 

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Not Confirming How Medicare Works Alongside Employer Health Plans

If you’re working past 65 and have employer-sponsored medical coverage, Medicare still matters. Roberts often sees people misunderstand how Medicare works alongside other coverage. “Employer plans and retiree coverage do not always function the way they did before age 65,” she says.

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Once you turn 65, find out from your employer whether you need to sign up for Part A or Part B. “Depending on employer size and plan rules, Medicare may be primary or secondary, and that order determines how claims are paid,” Roberts explains.

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Delaying Medicare Because of Other Plans

“Another common mistake is delaying Medicare because of COBRA or a retiree health plan,” Roberts says. “These types of coverage do not allow you to safely delay Medicare enrollment. It often results in lifelong late enrollment penalties or gaps in coverage.” (You can decline to enroll in Medicare entirely, but according to Heathline, doing so will require you to decline other monthly benefits such as Social Security, and you’ll also need to repay what you’ve already received.)

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Contact your health insurance provider for more information if you’re unsure whether to sign up for Medicare given your current coverage. If you have post-employment COBRA coverage, your next steps may vary. The U.S. Centers for Medicare & Medicaid Services provides specific guidelines based on your current coverage and has an easy quiz to help confirm next steps.

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Missing the Correct Enrollment Period

Another big mistake, according to Roberts, is missing your correct enrollment window. “Medicare has several enrollment periods every year, which can be confusing,” she says. “However, your Initial Enrollment Period is the most important one.” 

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Your Initial Enrollment Period begins three months before you turn 65 and lasts three months after, lasting seven months total. “There can be permanent penalties and gaps in coverage if a beneficiary doesn’t enroll within their allotted window and has other creditable coverage,” Roberts says. 

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Many people also miss their Medigap Open Enrollment window. Medigap is the additional coverage from private companies that you can purchase to fill gaps in Medicare. There is a onetime period when you can buy a Medigap plan without medical underwriting. Once that window closes, “the underwriter can decline you for health reasons unless you live in one of the few states with Guaranteed Issue rights, allowing residents to buy a Medigap without having to pass underwriting during certain times of the year,” Roberts says.

Research your Medicare enrollment window before you turn 65, and base your decisions on your current coverage. If you’re looking to switch Medigap plans, take this quiz offered by the U.S. Centers for Medicare & Medicaid Services to understand your options.

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Missing Your Yearly Review

Roberts advises reviewing Medicare every year. “A brief yearly review helps prevent unexpected costs and ensures coverage still fits your needs,” she says. 

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Renewals can happen automatically unless you make changes. “Each fall, beneficiaries receive an Annual Notice of Change (ANOC) outlining updates for the coming year,” Roberts explains. “Check your Annual Notice of Change that arrives in September and compare the full picture, deductibles, copays, and whether your specific medications and doctors are still covered.” She recommends changing if your plan is “dropping one of your important medications next year, your Advantage plan is dropping your doctor from its network, or your plan has a drastic increase in premiums.”

Featured image credit: © Pranithan Chorruangsak—iStock/Getty Images

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Nicole Pyles
Writer

Based in Portland, Oregon, Nicole Pyles is an experienced freelance writer who writes about home and kitchen, health and wellness, and more. She's written for a variety of outlets, including Better Homes and Gardens, Tom's Guide, Better Report, and more.

This article is for general informational purposes only.
Affiliate Disclaimer Medical Disclaimer Financial Disclaimer

Updated: September 18, 2024
Posted In: Wealth
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