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2026 Edition

Some Medicare mistakes cost you for life. Know them before your deadline does.

I put the 10 costly Medicare mistakes into one practical checklist, each with the official rule, the deadline, the real 2026 cost and the exact step that avoids it.

  • Catch the deadlines that quietly close, before a lifetime penalty is added to your bill
  • Walk into HR, Social Security or any plan with the exact questions instead of guessing
  • Help a parent get this right now, instead of discovering the mistake when it can no longer be fixed

$45.99 one-time payment · instant digital access

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Some Medicare mistakes cost you for life. Know them before your deadline does.

What is inside The Medicare Mistakes Checklist

1

Before You Start: The Clocks That Run Around Your 65th Birthday

  • How to Use This Book
  • Clock 1: The Initial Enrollment Period (IEP)
  • Clock 2: Special Enrollment Periods (SEPs)
  • Clock 3: The Medigap Open Enrollment Period
2

Mistake 1: Letting the Part B Initial Enrollment Period Pass

  • What the Initial Enrollment Period Actually Is
  • A Familiar Story
  • The Part B Late Enrollment Penalty, Explained Precisely
  • What This Looks Like in Real Dollars
3

Mistakes 2 and 3: Trusting the Wrong Employer Coverage

  • The 20-Employee Line That Decides Everything
  • Why the 20-Employee Rule Trips Up Reasonable People
  • When It's Not Your Job, But Your Spouse's
  • The Younger Spouse's Coverage Cliff
4

Mistake 4: Counting on COBRA or Retiree Coverage Instead of Part B

  • The Word That Trips Everyone Up: "Coverage"
  • Why COBRA and Retiree Plans Don't Count
  • What Happens When the Clock Starts Anyway
  • The Coverage Gap Nobody Warns You About
5

Mistake 5: Going Without Creditable Drug Coverage

  • The Penalty Nobody Explains Until It's Too Late
  • Why This Mistake Feels Invisible
  • What "Creditable Coverage" Actually Means
  • The Notice You're Supposed to Get Every Year
6

Mistake 6: Missing the Medigap Open Enrollment Window

  • What Medigap Actually Is, and Why the Timing Matters So Much
  • How the Six-Month Clock Actually Starts
  • What Guaranteed Issue Actually Means
  • A Composite Example: Two People, Two Timelines
7

Mistake 7: Choosing Medicare Advantage First Without Knowing the Way Back

  • Two Paths, One Door That Swings Differently Each Way
  • The 12-Month Trial Right: A Real Safety Net, But Only for Some
  • What Happens After the Trial Right Expires
  • Why This Isn't About Which Option Is Better
8

Mistakes 8 and 9: Being Surprised by IRMAA, and Not Appealing It

  • The Letter Nobody Budgeted For
  • How the Two-Year Lookback Actually Works
  • The 2026 Income Brackets, Structurally Explained
  • The One-Time Income Trap
9

Mistake 10: Keeping HSA Contributions Going After Medicare Starts

  • Why HSAs and Medicare Cannot Coexist
  • The Six-Month Trap That Makes This Mistake Different
  • Who This Actually Affects
  • The Official Rules, Plainly Stated
10

The 12-Month Deadline Planner: From Your 64th Birthday Onward

  • Age 64, Twelve Months Out: Gather and Verify
  • Eleven Months Out: The Employer Size Conversation
  • Ten Months Out: The Drug Coverage Check
  • Nine Months Out: COBRA and Retiree Coverage Reality Check
11

For Grown Children: Going Through It Together

  • Why This Has to Be a "With," Not a "For"
  • The Permissions You Need Before You Need Them
  • The One-Page Family Medicare Sheet
  • What Belongs to Your Parent Alone

About Susan

Susan · Narrator of the YouTube channel Medicare with Susan

Susan is the narrator of the YouTube channel Medicare with Susan. She is not a licensed agent, not a broker, and she sells no plans. This checklist puts the rules, deadlines and official 2026 figures from Medicare.gov, SSA.gov and CMS.gov into one place, so every decision around 65 is checked on paper before you sign anything. Rules and amounts can change every year - confirm your own dates with Social Security or your state's free SHIP counselor.

Susan

Does any of this sound familiar?

You are still working and assume you can wait

Employer coverage, COBRA, an HSA: each one changes what you must do at 65, and the rules are rarely explained up front.

Everyone gives you a different answer

HR says one thing, a plan salesperson another, a neighbor a third. Nobody puts the official rule and the deadline in front of you.

You are handling the paperwork for a parent

You want to protect them, but the letters, windows and acronyms pile up faster than you can check them.

“The expensive part of Medicare is rarely the choice itself. It is the deadline nobody told you about.”

Everything you need to turn 65 right

Part B Deadlines

The window that decides whether a penalty follows you.

Employer Coverage & COBRA

What still working really means for Medicare.

The Medigap Window

Why timing matters more than the plan itself.

Medicare Advantage First

What to check before choosing it as your first plan.

IRMAA & HSA

Income and savings decisions with a Medicare price tag.

For Grown Children

A guided page to go through it with a parent.

This checklist is for you if …

You are turning 65 soon

You want every rule and deadline in one place, before a window closes without warning.

You are still working past 65

You have employer coverage, COBRA or an HSA and need to know exactly what applies to you.

You handle the paperwork for a parent

You want a clear page to go through step by step together, so nothing slips.

Get The Medicare Mistakes Checklist today

Next offer starts in 05hrs12min43sec
The Medicare Mistakes Checklist
2026 Edition
  • The 10 Medicare mistakes that cost for life, each with the official rule and deadline
  • The real 2026 cost of each mistake, with sources from Medicare.gov, SSA and CMS
  • A tick-off checklist for every mistake
  • The exact questions to ask HR, Social Security and any plan
  • A 12-month deadline planner starting at your 64th birthday
  • A page for grown children to go through it with a parent
  • Instant access on any device
$45.99

Digital checklist book (PDF) · one-time payment · the 2027 edition is updated once CMS publishes the 2027 amounts

Secure paymentInstant accessReceipt by email

What you will discover

  • The deadline most people learn about too late
  • Why still working does not always mean waiting
  • The one window you cannot reopen later
  • What to ask before choosing Medicare Advantage
  • How your income quietly changes your premium
  • The HSA detail that surprises people near 65
  • The COBRA assumption that can cost for life
  • The question HR often does not answer
  • Which mistakes can still be fixed, and which cannot
  • What to check with a parent this month

Frequently asked questions

I am still working. Is this relevant for me?

Yes. Employer coverage, COBRA and an HSA each have their own chapter, with the official rule, the deadline and the questions to ask HR.

Do you sell Medicare plans or earn commissions?

No. I sell no plans and receive no commissions. The checklist is educational and points you to the official sources so you can verify every rule yourself.

Where do the figures come from?

Only from official sources such as Medicare.gov, SSA and CMS, and each figure is marked with its source. The 2027 edition is updated when CMS publishes the 2027 amounts.

Can I use it for a parent?

Yes. There is a dedicated page for grown children to go through the checklist together with a parent, step by step.

In what format do I get it?

As a PDF checklist book, readable and printable on computer, tablet and phone.

How do I receive it after purchase?

Right away by email, with a secure personal download link.

The Medicare Mistakes Checklist $45.99