Most people spend more time researching a new phone than they do their Medicare coverage. That’s not a criticism — Medicare is complicated, the rules aren’t obvious, and nobody hands you a clear roadmap when you turn 65. But the cost of getting it wrong can follow you for years, sometimes for the rest of your life.
This post covers the most common Medicare mistakes we see here in Florida — the ones that lead to late enrollment penalties, coverage gaps, surprise bills, and plans that don’t actually work for how you live. If you’re new to Medicare or thinking about making a change, read this before you do anything else.
Mistake #1: Missing your Initial Enrollment Window
Medicare has a 7-month Initial Enrollment Period (IEP) that surrounds your 65th birthday — three months before, the month of, and three months after. Miss it without a qualifying reason and you could face a lifetime late enrollment penalty on Part B, plus a gap in coverage until the next General Enrollment Period.
This is one of the most expensive mistakes a person can make, and it happens more often than you’d think — especially for people who are still working at 65 and assume they’ll “just sign up later.” The rules around employer coverage and Medicare coordination are specific, and assuming you’re covered when you’re not is a costly assumption.
If you’re approaching 65 and not sure where you stand, start at our Medicare 101 page for a straightforward breakdown of the parts, timelines, and what you actually need to do.
Mistake #2: Not Understanding What Medicare Does and Doesn’t Cover
Original Medicare — Parts A and B — covers a lot, but it doesn’t cover everything. There are no out-of-pocket maximums. There’s no routine dental, vision, or hearing coverage. Prescription drugs aren’t included unless you add a Part D plan. Foreign travel emergencies aren’t covered.
People are often shocked by their first major medical bill on Medicare because they assumed “Medicare covers it.” Understanding the gaps before you need them is the difference between being prepared and being blindsided.
This is exactly why the decision between a Medicare Supplement (Medigap) plan and a Medicare Advantage plan matters so much. They solve the coverage gap in very different ways, and the right answer depends entirely on your situation. If you haven’t thought through that decision yet, our plan selector at compare your plan options is a good place to start.
Mistake #3: Choosing a Plan Based on the Premium Alone
The lowest premium is not the lowest cost. This is probably the single most repeated mistake we see, and it makes sense on the surface — if Plan A costs $0 and Plan B costs $180 a month, Plan A looks like the obvious winner.
But Medicare Advantage plans with $0 premiums often come with copays, prior authorization requirements, network restrictions, and out-of-pocket maximums that can reach $8,000 or more in a bad year. A Medigap plan with a higher monthly premium may cost you far less if you use your coverage regularly.
The right question isn’t “what’s the cheapest plan?” It’s “what will this plan actually cost me based on how I use healthcare?” Those are very different calculations.
Mistake #4: Not Checking if Your Doctors Are in Network
This one catches people every single year, especially in Florida where Medicare Advantage enrollment is high. If you choose a Medicare Advantage HMO plan, your coverage is generally limited to doctors and hospitals inside that plan’s network. Your current primary care physician, your cardiologist, your preferred hospital — none of that is guaranteed to be covered.
Before you enroll in any Medicare Advantage plan, verify that your doctors are in network for that specific plan, for that specific year. Networks change annually. A doctor who was in-network in 2024 may not be in 2025.
If keeping your current doctors is a priority, a Medicare Supplement plan paired with Original Medicare may give you more flexibility — you can see any doctor in the country who accepts Medicare, no network required.
Mistake #5: Ignoring Part D (Prescription Drug Coverage)
Skipping Part D because you don’t take many medications right now is a mistake that can cost you later. If you go without creditable prescription drug coverage for 63 or more consecutive days after your Initial Enrollment Period, you’ll face a Part D late enrollment penalty that gets added to your premium permanently.
Beyond the penalty, drug coverage matters more as you age. Locking in a plan early — even a basic one — protects you from the penalty and ensures you have coverage when you need it most.
Mistake #6: Picking a Plan Without Reviewing It Every Year
Medicare plans change every October 1st, with those changes taking effect January 1st. Premiums go up. Formularies change. Networks shift. A plan that worked well for you last year might not be the best fit this year.
The Annual Enrollment Period (AEP) runs October 15 through December 7 every year. That window exists for a reason — it’s your opportunity to review what changed and make adjustments if needed.
We do annual reviews with every client at Capstone Health. It’s one of the most important things we do because staying on the wrong plan for years is one of the quieter, slower Medicare mistakes — you don’t always see the cost until it’s added up.
Mistake #7: Working With an Agent Who Disappears After Enrollment
This one isn’t talked about enough. A lot of people in Florida get enrolled by someone they met at a seminar, a kiosk at a big box store, or through a call center — and then never hear from that person again.
Medicare isn’t a one-time transaction. Your needs change. Plans change. Life changes. Having an agent who is available year-round, who knows your situation, and who proactively reaches out before AEP every year is part of how you avoid the mistakes on this list year after year.
If you’re in Pasco, Pinellas, Hernando, or Hillsborough County and you want a local agent who picks up the phone, that’s exactly what we do at Capstone Health. Our office is in New Port Richey, and we work with clients across Florida.
Just Getting Started with Medicare?
If you’re new to Medicare and this list feels overwhelming, that’s completely normal. Start with the basics — our new to Medicare page walks you through what you need to know, in plain language, before you make any decisions.
You don’t have to figure this out alone, and you definitely don’t have to figure it out from a TV commercial.
Frequently Asked Questions
What is the most common Medicare mistake people make? Missing the Initial Enrollment Period is one of the most costly mistakes because it can result in lifetime late enrollment penalties on Part B and gaps in coverage. Many people who are still working at 65 delay enrollment assuming their employer coverage protects them, without verifying how their specific plan coordinates with Medicare.
What happens if you miss the Medicare enrollment deadline? If you miss your Initial Enrollment Period without a qualifying Special Enrollment Period, you may have to wait until the General Enrollment Period (January 1 through March 31) to sign up for Part B, with coverage starting July 1. You may also face a permanent Part B late enrollment penalty of 10% for each 12-month period you were eligible but didn’t enroll.
Is a $0 premium Medicare Advantage plan a good deal? Not always. A $0 premium plan can still come with significant out-of-pocket costs in the form of copays, coinsurance, and out-of-pocket maximums that can reach thousands of dollars. The premium is only one piece of the total cost picture.
Do I need a Part D plan if I don’t take any medications? Generally yes, unless you have other creditable drug coverage. Going without Part D for 63 or more consecutive days after your Initial Enrollment Period can result in a permanent late enrollment penalty added to your monthly premium.
Can I change my Medicare plan after I enroll? Yes. The Annual Enrollment Period (AEP) from October 15 to December 7 each year allows you to switch Medicare Advantage or Part D plans. There are also Special Enrollment Periods triggered by qualifying life events. A licensed Medicare agent can help you understand your options and timing.
How do I avoid Medicare mistakes in Florida? Work with a licensed, independent Medicare agent who represents multiple carriers and is available year-round — not just during enrollment season. Florida has high Medicare Advantage enrollment, competitive plan options, and county-specific plan availability, which makes having a knowledgeable local agent especially valuable.
Capstone Health is an independent Medicare insurance agency located in New Port Richey, Florida, serving Pasco, Pinellas, Hernando, and Hillsborough Counties and across the state. Will Smith has been a licensed Medicare agent since 2005. We represent a wide range of Medicare plan options and provide free, no-obligation consultations year-round. Looking for guidance on what to look for in a local Medicare agent near you? We put together a complete guide.