Medicare Enrollment: 3 mistakes to avoid when aging into Medicare

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By Whitney Stidom, Vice President of Consumer Enablement, eHealth 

More Americans are born during August than any other month, which means more people are aging into Medicare now than at any other point in the year.  Across the country, as many as 11,000 Americans become Medicare-eligible every day. 

While turning 65 and becoming eligible for Medicare is a major life milestone, 75% of beneficiaries say choosing coverage is confusing. That’s in part because new enrollees must quickly understand whether their doctors, pharmacies, hospitals and facilities are in network, how much they might pay out of pocket for medical care and prescription needs, and the key differences between the various Medicare coverage options.  

If you or a loved in will soon be celebrating a 65th birthday and aging into Medicare, avoiding the following three mistakes can help improve access to care, reduce the risk of surprise medical costs, and contribute to overall well-being.  

Mistake #1: Missing your initial Medicare enrollment window 
Your initial election period under Medicare typically begins three months before you turn 65, includes your birth month, and extends three months afterward. Missing the initial enrollment period can lead to delayed or denied coverage and financial penalties that last a lifetime.  

For instance, if you miss the initial enrollment period and then decide to add a Medicare Supplement plan, you can be declined coverage or charged more based on your medical history. If you stick with Original Medicare, enrolling late in Medicare Part B can result in paying lifetime surcharges on your premiums, starting at about $240 more per year (in 2026) and going up from there depending on the length of the delay.  

Unfortunately, a recent survey of people approaching Medicare age (55 to 64) found most are unaware of these potential penalties. It’s important to mark key enrollment dates on your calendar before your 65th birthday and understand whether your employment status or employer coverage may affect your Medicare enrollment timeline. 

Mistake #2: Ignoring prescription drug coverage  
Some people think Medicare automatically covers prescription drugs, but that is not the case. Others may incorrectly assume they can sign up for prescription drug coverage whenever they need it, without consequences. 

The truth is that delaying enrollment in Medicare Part D drug coverage or letting prescription drug coverage lapse can become more expensive later. Medicare may impose a late-enrollment penalty if you go too long without creditable prescription drug coverage after becoming eligible for Medicare. That penalty continues for as long as you remain enrolled in a Medicare Part D plan, starting at about $56 extra per year (in 2026) for every year you went without Medicare drug coverage.  

Even if you rarely visit a pharmacy today, prescription needs can change unexpectedly, and the risk of developing chronic conditions increases by age. In fact, 88% of Americans 65 and older take at least one prescription medication. Evaluating your drug coverage options when you first become eligible may help protect both your health and your future budget. 

Mistake #3: Mismatching your Medicare plan with your lifestyle & budget 
Do you know the difference between Original Medicare, Medicare Advantage, Medicare Supplement, and Part D? If not, you are not alone: Research shows just 13% of current Medicare enrollees can correctly identify the definition for all of these.  

Educating yourself about your Medicare plan options before you enroll can help you find the best match for your budget and lifestyle. While Original Medicare (Parts A and B) helps pay for hospital and doctor care, it leaves beneficiaries responsible for out-of-pocket expenses and lacks prescription drug coverage. 

To fill those gaps, more people are enrolling in Medicare Advantage, which bundles Medicare Parts A and B into a plan offered by a private insurer. Most of these plans include prescription drug coverage and an annual cap on out-of-pocket costs, and many include benefits such as dental, vision, and hearing care. The other option is a Medicare Supplement (Medigap) plan, which works alongside Original Medicare and can reduce out-of-pocket medical expenses. Multiple factors, including your current health status, ability to pay monthly premiums, and travel plans, will help determine which coverage option is a better option for you. 

By better understanding eligible enrollment dates and plan options, turning 65 can be a reason for celebration while providing the opportunity to make the right health plan coverage decision for you.         

Whitney Stidom is vice president of consumer enablement at eHealth, an online health insurance marketplace that helps consumers navigate their health benefit decisions