The 5 Most Expensive Medicare Mistakes (and How to Avoid Them)

October 1, 2025
Posted in Blog
October 1, 2025 TouchCare Team

Look, Medicare isn’t exactly light reading. Between Parts A, B, C, and D, plus Medigap and all those enrollment windows, it’s like trying to solve a puzzle where someone keeps changing the pieces. And here’s the thing: one wrong move can cost you thousands of dollars. Not just this year, but potentially for the rest of your life.

So let’s talk about the five mistakes that hit people’s wallets the hardest. Because honestly? Most of them are completely avoidable once you know what to watch for.

Missing Your Initial Enrollment Window (The Gift That Keeps Taking)

You know what’s sneaky? The Medicare enrollment period doesn’t work like you’d think. You’ve got a seven-month window that starts three months before your 65th birthday. Sounds reasonable, right? But here’s where people get tripped up: if you’re still working and covered by your employer’s plan, you might think you can wait. Sometimes you can. Sometimes you absolutely cannot.

Miss that window without qualifying for a Special Enrollment Period, and you’re looking at a Part B penalty of 10% for every 12-month period you were eligible but didn’t sign up. That penalty? It lasts forever. We’re talking about an extra chunk of change coming out of your Social Security check month after month, year after year. The math gets ugly fast.

The worst part is people usually discover this penalty exists right when they’re trying to enroll later. Talk about a rough surprise.

What to do instead: Mark your calendar three months before your 65th birthday. Even if you think you don’t need Medicare yet, at least check with your HR department or a Medicare counselor. Get it in writing whether your employer coverage counts as “creditable coverage.” That documentation could save you serious money down the road.

Sticking with Original Medicare When You Need More (Or Vice Versa)

Here’s where it gets personal. Original Medicare (Parts A and B) covers a lot, but it doesn’t cover everything. No prescription drug coverage. No out-of-pocket maximum. And those 20% coinsurance amounts? They can add up faster than you’d believe, especially if you have a health scare.

But here’s the flip side, and this is important: Medicare Advantage plans aren’t automatically better just because they often cost less upfront. Sure, you might pay $0 premium, but you’re dealing with provider networks. Need to see a specialist across town? Better check if they’re in-network first. Want to spend winters in Arizona? Make sure your plan works there.

I’ve seen people choose based purely on monthly premium, which is like buying a car because you like the color. It might work out great, or you might end up with something totally wrong for your lifestyle.

What to do instead: Think about how you actually use healthcare. Do you see a lot of specialists? Travel frequently? Have a bunch of prescriptions? Match your plan to your life, not the other way around. And remember, you get another chance during Annual Enrollment Period each fall to switch things up if your needs change.

Skipping Part D Because You Don’t Take Many Meds

Let me paint you a picture. You’re 65, healthy, maybe taking one or two generic medications that barely cost anything. So why pay for Part D prescription coverage, right?

Wrong. So wrong.

Even if you don’t enroll in Part D when you’re first eligible, you’ll pay a late enrollment penalty of 1% of the national base premium for every month you went without coverage. And just like the Part B penalty, this one sticks around. Maybe you don’t need much now, but what about in five years? Ten years? When you actually need that coverage, you’ll be paying more for it than you should be.

Plus, and this catches people off guard, health changes fast. One diagnosis, one new prescription regimen, and suddenly that “I don’t need drug coverage” decision feels pretty short-sighted.

What to do instead: Get Part D coverage when you’re first eligible, even if it’s a basic plan. You’re paying for the insurance of not having a penalty later. Think of it like car insurance; you hope you won’t need it, but you’d never drive without it.

"Original Medicare (Parts A and B) covers a lot, but it doesn’t cover everything. No prescription drug coverage. No out-of-pocket maximum. And those 20% coinsurance amounts? They can add up faster than you’d believe, especially if you have a health scare."

Choosing Plans Based on Premium Alone

This one’s related to what I mentioned earlier, but it deserves its own spotlight because it’s such a common trap. You see a plan with a $0 premium or a really low number, and it looks like a no-brainer. But premiums are just the entry fee.

What about copays? Coinsurance? Deductibles? Maximum out-of-pocket limits? Does the plan cover your specific medications, and if so, at what tier? Is your doctor in-network? Your hospital?

A plan that costs $50 more per month but has a $3,000 lower out-of-pocket maximum could save you thousands if you actually need medical care. And let’s be real: we’re talking about Medicare here. The chances of needing medical care aren’t exactly low.

What to do instead: Look at total potential costs, not just the premium. Add up what you’d pay in a typical year, then (and this is key) figure out what you’d pay in a bad year. Because bad years happen. The cheapest premium often comes with the most expensive care.

Forgetting About Medigap Enrollment Rights

Medigap (or Medicare Supplement Insurance, same thing) can be a lifesaver. It fills in those gaps Original Medicare leaves behind. But here’s what makes this mistake so costly: you have guaranteed issue rights during specific periods, mainly your Medigap Open Enrollment Period, which runs for six months starting when you’re 65 and enrolled in Part B.

During that window, insurance companies can’t turn you down or charge you more because of health conditions. It’s your golden ticket. Miss it, though, and you’re subject to medical underwriting. That means they can reject you, charge you more, or exclude coverage for pre-existing conditions. Some people can’t get Medigap coverage at all outside these protected periods.

It’s not just about having coverage. It’s about having coverage you can actually afford and that actually covers you when you need it.

What to do instead: If you’re going with Original Medicare and want the security of a Medigap plan, don’t sleep on that six-month window. Research plans, compare prices, and enroll during your Open Enrollment Period. Your future self (the one who doesn’t have to drain savings to pay medical bills) will thank you.

The Bottom Line? Knowledge Really Is Money

Look, Medicare doesn’t have to be this complicated. But it is, at least right now. And the consequences of mistakes aren’t just annoying; they’re expensive. Really expensive. For a long time.

The good news? You’re already ahead of the game by reading this. Seriously. Most of these mistakes happen because people don’t know what they don’t know. Now you know what to watch for.

Take the time to understand your options. Ask questions. Get help from someone who knows the system. And remember: the “easiest” choice isn’t always the right choice. Sometimes you need to put in a little extra effort upfront to save yourself a lot of headaches and money later.

You Don’t Have to Figure This Out Alone

Here’s something you might not realize: as a TouchCare member, you’ve got access to Medicare experts who actually know their stuff. We’re talking specialists with at least five years of experience navigating Parts A, B, C, and D, who stay on top of every state and federal regulation change. More importantly? They treat this like the big deal it is.

Our concierge team provides personalized consultations that go way beyond generic advice. They’ll help you compare Medicare Advantage and Medigap plans, track your eligibility timelines, and answer those specific questions that keep you up at night. No pressure, no sales pitch, just unbiased guidance tailored to your actual situation.

Whether you’re approaching 65 or trying to fix a mistake from years ago, TouchCare’s Medicare support makes the whole process less overwhelming. Because your Medicare decisions matter for your health and your financial security. Let us help you get them right.

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