About to turn 65? Avoid the 5 most common Medicare mistakes — enrollment timing, Part B, drug coverage penalties, and more — before they cost you.

August 31, 2026

Andrew Faligowski

Turning 65 Soon? Stop Doing These 5 Medicare Things

Agents Impact · Medicare Guide (503) 668-6100

For anyone within a year of 65

Turning 65 soon? Stop doing these five Medicare things.

A few habits quietly cost new Medicare enrollees money and coverage every year. None of them are your fault — the system just wasn't built to explain itself. Here's what to drop before your birthday hits.

Most people don't get Medicare wrong because they weren't paying attention. They get it wrong because nobody tells them the deadlines, the penalties, or the fine print until after it matters.

These five habits show up again and again in the months before someone's 65th birthday. Catch them early and the rest of the process gets a lot simpler.

Waiting until your birthday month to start looking

Your Initial Enrollment Period actually opens three months before you turn 65 and closes three months after — seven months total. Wait until the month of, and you've already burned half your window.

Do this instead

Start comparing options at least three months before your birthday, even if you don't plan to enroll right away.

Assuming your employer plan means you can skip Part B

If your employer has fewer than 20 employees, Medicare typically expects to become your primary coverage at 65 regardless of your job plan. Skip enrolling and you can be left with unpaid claims and a late penalty later.

Do this instead

Check your employer's size and plan rules directly with HR before deciding to delay Part B.

Choosing a plan by premium alone

The cheapest monthly premium can hide a narrow provider network or a drug formulary that doesn't include what you actually take. The real cost shows up the first time you need care.

Do this instead

Check that your doctors and prescriptions are covered before comparing prices between plans.

Going without drug coverage because you don't take medication yet

Part D has a permanent late enrollment penalty for every month you go without "creditable" drug coverage after you're first eligible — and it follows you for as long as you're on Medicare.

Do this instead

Enroll in a low-cost Part D plan even if you rarely need prescriptions now — it protects you later.

Skipping the Advantage-vs-Supplement decision until later

You typically get a one-time window with guaranteed acceptance into a Medicare Supplement plan, regardless of health history. Miss it, and insurers can ask health questions — or turn you down — if you try to switch afterward.

Do this instead

Compare Medicare Advantage and Medicare Supplement side by side while your enrollment window is still open.

Let's make sure none of these apply to you.

Get a free consultation Call (503) 668-6100

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Turning 65 Soon? Stop Doing These 5 Medicare Things

Turning 65 soon? Stop doing these five Medicare things.

Waiting until your birthday month to start looking

Assuming your employer plan means you can skip Part B

Choosing a plan by premium alone

Going without drug coverage because you don't take medication yet

Skipping the Advantage-vs-Supplement decision until later

Let's make sure none of these apply to you.

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What My Clients Are Saying

John S.

Above and Beyond

Sharon H.

Attentive and responsive

Janet F.

making a positive impact

Mark K.

all the stars

Aaron T.

Invaluable Expertise

Jordan R.

Exceptional Service

How It Works

Talk to Agent

Choose Your Plan

Book a Meeting

Get Treatment

Ready to shop for Health Insurance Plans in Oregon?

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