Are you at risk of a costly Medicare mistake?
Missing a deadline or picking the wrong plan can cost you for the rest of your life — through lifelong penalties or coverage you can’t easily change. Find out which mistakes you’re most at risk of, in about a minute.
The wrong move on Medicare can follow you for life.
Medicare has a handful of traps that catch people every year — and some of them come with a penalty you pay every month, forever. Others quietly lock you into coverage that’s hard to change later. The good news? Almost every one of them is completely avoidable if you know it’s coming.
This page helps you spot your personal risks before they cost you — then points you to the exact tools and free help to avoid them. Start with the checker below.
Which situation sounds most like you?
Tap the one that fits — you’ll instantly see the mistakes you’re most at risk of, and how to avoid them. Your answer appears on the right.
Turning 65 soon
- ●Missing your Initial Enrollment Period. Sign up on time or you can face a lifelong Part B penalty. See the windows.
- ●Assuming Medicare is automatic. For most people it isn’t — you usually have to enroll yourself.
- ●Skipping drug coverage. No Part D when you’re first eligible can mean a permanent penalty.
Still working past 65
- ●Delaying Part B when you shouldn’t. With a small employer, delaying can be a costly mistake.
- ●Trusting COBRA or retiree coverage. These don’t let you delay Part B — a very common trap.
- ●Missing your Special Enrollment Period when you leave the job. See employer rules.
Choosing a plan now
- ●Picking a plan your doctors don’t take. Always confirm your providers first.
- ●Ignoring your drug costs. The wrong drug plan can cost hundreds a year. Price your meds.
- ●Choosing on premium alone without weighing the out-of-pocket gap.
Already enrolled, want to review
- ●Never re-shopping. Plans and prices change yearly — set-and-forget can cost you.
- ●Missing the Annual Enrollment Period (Oct 15 – Dec 7) to make changes.
- ●Not knowing your rights to switch. A free review often finds savings.
On disability or under 65
- ●Not knowing you may qualify. Medicare isn’t only for 65+. Check eligibility.
- ●Missing special rules for SSDI, ALS, or ESRD that change your timing.
- ●Overlooking ACA coverage as a bridge if you’re not yet eligible.
Not sure which risks apply to you? Let’s check together.
A licensed May River advisor will review your situation and catch any mistakes before they cost you — free, and with no pressure.
The 6 most common Medicare mistakes.
These catch people every year. Knowing them is how you avoid them.
Missing your enrollment window
Sign up late for Part B and you can pay a penalty every month for the rest of your life.
Trusting COBRA to hold you over
COBRA and retiree plans don’t let you delay Part B — a costly and common misunderstanding.
Picking a plan your doctor drops
Not confirming your doctors and medications are covered before enrolling.
Choosing on price alone
The cheapest premium can leave you exposed to big out-of-pocket costs later.
Skipping drug coverage
No Part D when first eligible can mean a permanent late-enrollment penalty.
Never reviewing again
Set-and-forget. Plans change yearly, and a quick review often finds real savings.
Tools that help you avoid every one of these.
Use these free, no-login tools to check yourself — or let a licensed advisor do it with you.
Find My Medicare Match
Answer a few questions and get a personalized recommendation on the right path.
Take the quizDrug Coverage Calculator
Check how your medications are covered so drug costs never surprise you.
Price my drugsEnrollment Periods
Know every window so you never miss a deadline or trigger a penalty.
See the windowsHow to Choose a Plan
Weigh Supplement vs Advantage against your doctors, drugs, and budget.
Choose a planMedicare Costs
See the 2026 numbers and the IRMAA income surcharge before you commit.
Understand costsCalculator & Planning Tools
Estimate your total Medicare costs and compare your options side by side.
Open the toolsMistake & penalty questions.
What is the biggest Medicare mistake people make?
Is the Part B late penalty really for life?
Does COBRA count as coverage so I can delay Part B?
Can I fix a Medicare mistake after it happens?
How do I make sure I don’t make one of these mistakes?
Let’s catch your risks before they cost you.
A licensed May River advisor reviews your situation, spots any mistakes, and helps you avoid them — free, no pressure, and your advocate for life.
(843) 227-6725