Real stories, real regrets—and how to avoid them

“I had no idea Medicare could be this confusing.”

That’s something I hear all the time.

For most people, turning 65 should feel like a win—you’ve worked hard, paid into the system, and now you’re finally eligible for Medicare. But instead of peace of mind, many people feel overwhelmed by deadlines, plan choices, confusing terminology, and unexpected costs.

I’ve been helping people enroll in Medicare for over 20 years, and I’ve seen firsthand how easy it is to make mistakes—some small, some costly, and some that lock you into coverage you didn’t really understand.

Recently, I asked the Reddit community in r/Medicare what they thought the most common or painful Medicare mistakes were. I heard from retirees, adult children helping their parents, fellow agents, and even folks who made a mistake and learned the hard way.

This post brings together both expert advice and real-world stories—so you can avoid the pitfalls others wish they had known about sooner.

Let’s start with one of the biggest (and most tempting) traps…

1. Choosing a Medicare Advantage Plan Just Because It’s “Free”

Let’s face it - when you're comparing plans and see a big bold $0 premium, it’s hard not to look twice. On paper, those Medicare Advantage plans sound fantastic: dental, vision, gym memberships, all wrapped up with no extra monthly cost.

But as many Reddit users (and a whole lot of my clients) can attest, that zero-dollar premium can come with hidden costs.

One user wrote:
“The biggest mistake is getting lured into an Advantage plan just because it has a $0 premium. It took me one year and two denied procedures to realize the true cost.”

Before enrolling in a plan based on premium alone, take a few minutes to compare Medicare Advantage plans near me using Medicare’s plan finder or by speaking with a local advisor who understands your area’s provider networks.

I had a client—let’s call him 'Frank'—who was on a Medicare Advantage plan with no premium and a long list of extras. It worked great... until he needed physical therapy after a fall. Suddenly, those co-pays added up fast, and he found out that his therapist wasn’t in-network.

What many people don’t realize is that Medicare Advantage plans often:

• Have restricted networks
• Require prior authorizations
• Come with higher out-of-pocket costs if you get sick or need specialist care

Sure, they can work well for some people—but choosing a plan based solely on the premium without understanding the coverage is one of the most common and costly mistakes.

2. Missing the Medigap Enrollment Window

Before deciding between Medicare Advantage and Medigap, it’s important to ask: What does Medigap cover, and how does it differ from the other options? Many Reddit users realized too late that the plans are not interchangeable.

This is one of those Medicare rules that doesn’t get talked about enough—until it’s too late.

When you first enroll in Medicare Part B, you get a 6-month Medigap open enrollment window. During that time, you can get a Medicare Supplement plan (also called Medigap) with no medical underwriting. That means they have to accept you—no questions asked about your health history.

But once that window closes? All bets are off.

One Redditor said:
“I waited too long to decide between Advantage and Medigap. When I went to apply for a Supplement, they asked about my heart condition and rejected me. I had no idea that was even a thing.”

I’ve seen this more times than I’d like to admit. I worked with a woman named Linda who originally chose a Medicare Advantage plan because of the low premium. A year later, after some unexpected health issues, she wanted the freedom of a Medigap plan—no referrals, no networks.

But because she was now outside of that six-month window, she had to go through underwriting. Her recent hospital stay disqualified her from several plans, and the ones that would accept her came with sky-high premiums.

She told me, “If I’d known there was a clock ticking, I never would’ve waited.”

That six-month window? It’s one of the most powerful decision points in your Medicare journey. If you miss it, switching to a Medigap plan later becomes a gamble—not a guarantee.

That’s why so many people who miss their Medigap window end up stuck with coverage they didn’t really want. If you’re considering a Supplement plan, now is the time to explore the best Medicare Supplement plans for 2025 before your guaranteed issue rights expire

Quick Breakdown: What You Need to Know

• Your Medigap open enrollment window starts when you’re 65 or older and enrolled in Part B
• During this time, insurance companies must accept you
• After that, they can deny you or charge more based on your health
• This is not the same as the Fall Open Enrollment window

So if you’re thinking about Medigap—or even just want to keep your options open—make sure you’re looking at it as soon as you enroll in Part B. Don’t wait until a health issue forces your hand.

3. Thinking COBRA or Employer Coverage Lets You Delay Medicare

This is one of the most confusing—and costly—areas of Medicare enrollment. It trips up a lot of people who are retiring a little later or who have access to benefits through a spouse or former employer.

One Reddit user summed it up perfectly:
“People think COBRA means they don’t have to enroll in Medicare. It doesn’t. And then the penalties hit.”

Let’s break this down because it’s not just a paperwork mistake—it can cost you for life.

COBRA ≠ Medicare Credit

If you’re 65 or older and you have access to COBRA, it might seem like a good option for staying insured while you figure things out. But the key thing to know is:

COBRA is not considered "creditable coverage" for delaying Medicare Part B.

That means if you don’t sign up for Medicare when you’re supposed to—and you rely solely on COBRA—you could face:

• A Part B late enrollment penalty (which lasts for life)
• A gap in coverage (COBRA might drop you once they find out you didn’t enroll in Medicare)
• A Part D penalty, too, if you’re not enrolled in drug coverage

Real Story: Jim’s Costly Delay

I had a client named Jim who retired at 66. His employer offered COBRA, and it looked solid. So he declined Medicare Part B and stuck with COBRA for 18 months.

When he came to me a year and a half later, his COBRA was ending—and that’s when we realized the problem.

He was outside his Initial Enrollment Period and didn’t qualify for a Special Enrollment Period because COBRA didn’t count. That meant:

• He had to wait months before he could enroll in Part B
• He would pay a 10% penalty on his premium for every year he delayed
• His Medigap options were severely limited

Jim looked at me and said, “No one told me this. I thought I was being smart.”

What to Do Instead:

• If you’re still working and have group coverage through an employer with 20+ employees, you can delay Medicare Part B without penalty
• But COBRA, retiree coverage, or smaller employer plans don’t count
• Always double-check with a Medicare advisor or call Medicare directly if you’re unsure

The bottom line? Don’t assume your current coverage lets you wait. COBRA doesn’t protect you from Medicare penalties.

4. Assuming One Source Has All the Answers

When you’re new to Medicare, it’s totally natural to want someone to just tell you what to do. I get it—there’s a sea of brochures, comparison charts, mailers, TV ads, and a dozen different websites with different advice.

But here’s the truth that came through loud and clear on Reddit—and it mirrors what I tell my clients every day:

“No one person and no one source has all the answers.”

Why It’s a Problem:

People often:

• Rely entirely on one agent or broker (sometimes even one who only represents a single company)
• Only talk to friends who "liked their plan"—without realizing how different their needs are
• Use just one website, like Medicare.gov, but don’t fully understand how to interpret the plan comparisons

This creates blind spots. And in Medicare, a blind spot can cost you more than just money — it can mean losing access to your doctor, missing a deadline, or getting stuck in a plan that doesn’t meet your needs.

Real Example: Carol's Confusion

Carol (not her real name) came to me after enrolling in a Medicare Advantage plan her friend recommended. The friend loved it because it covered her gym membership and had no premium.

But Carol was on five medications, saw a specialist every month, and needed a knee replacement in the next year. Her plan? Not great for any of that.

She said, “I didn’t know there were other options. I just figured they were all the same.”

She was shocked when we looked at her drug costs and discovered she could’ve paid hundreds less per year with a different plan. She had made a well-intentioned decision—but without the full picture.

How to Get a More Complete View:

• Use multiple resources: Medicare.gov, SHIP counselors, and licensed independent brokers
• Ask more than one person—especially if they have different health needs than you
• Don’t assume what works for someone else will work for you

Think of it like getting a second opinion before a major surgery. It doesn’t hurt to double-check—and it could save you time, money, and frustration later.

Reddit users shared personal stories that went far beyond what you'd find in typical Medicare plan reviews and ratings—which is why getting advice from multiple sources can make such a difference.

5. Not Reviewing Coverage Annually

This one might be the easiest mistake to make, simply because it’s so tempting to stick with what’s familiar.

I can’t tell you how many times I’ve heard a client say, “My plan worked great last year, so I just let it renew.” And I get it—Medicare can be overwhelming, and if things seem okay, why rock the boat?

But here’s the thing: Medicare Advantage Plans (Part C) and Prescription Drug Plans (Part D) change every year.
And what worked well for you last year may not be the best fit this year.

One Redditor said it perfectly:
“Not reviewing your coverage every fall is like blindly signing a contract each year without reading it. You could be agreeing to higher drug prices or losing your doctor and not even know it.”

The Truth About Annual Enrollment (Oct 15 – Dec 7):

Every fall, Medicare gives you a chance to:

• Switch drug plans
• Move between Medicare Advantage plans
• Return to Original Medicare
• Reevaluate your pharmacy network and medication coverage

Your prescriptions may move to a different tier, or your pharmacy could drop from the preferred network. Tools like the Medicare Part D cost calculator can help you estimate your total yearly drug costs before it’s too late.

Yet many people skip it—either because they don’t know it exists or because they assume “no news is good news.”

💡 Real Story: Janet’s Surprise Drug Bill

Janet was a longtime client of mine who had been happy with her Medicare Advantage plan for years. But one January, she called me in a panic—her Eliquis prescription had nearly doubled in price.

We looked into it and sure enough: her plan’s formulary had changed, and Eliquis had been bumped to a higher tier.

She said, “I had no idea my plan could just change like that.”

How to Avoid This Pitfall:

• Mark your calendar for October 15th every year
• Make a list of your current medications and providers
• Use Medicare’s Plan Finder or talk to an advisor to compare what’s changed
• Don’t assume your plan is still the best—it might not be

Spending just an hour or two reviewing your plan each fall can save you hundreds—sometimes even thousands—in the year ahead. It’s a small investment of time with a big return in peace of mind.

Conclusion: Learn From Their Mistakes—So You Don’t Have to Repeat Them

If there’s one thing we can take from the stories shared by real people on Reddit—and from the hundreds of clients I’ve worked with—it’s this:

Most Medicare mistakes don’t come from bad decisions.
They come from rushed choices, incomplete information, or not knowing what questions to ask.

Learning how to choose a Medicare plan is one of the smartest things you can do before your 65th birthday. The wrong choice today could cost you thousands later.

The good news? You don’t have to go through it blindly.
Whether it’s avoiding the surprise cost of a “$0 premium” plan… enrolling in Medigap at the right time… or simply reviewing your coverage each year—a little preparation goes a long way.

If you’re turning 65 soon, or helping someone who is, take this article as a nudge:

• Ask questions.
• Compare your options.
• Don’t be afraid to get a second opinion.

At Lehigh Partners Senior Benefits, we’re here to guide—not push. If you ever want help understanding your Medicare choices, we’d be glad to walk you through them at your pace, in plain English.

If you’re still unsure which direction to take, there’s no shame in asking for Medicare enrollment help near me. Talking to someone local who understands the rules can save you a lot of stress.

You can explore more helpful resources at
👉 https://lehighpartners.net/blog/