Free 1-page checklist

Turning 65? Don't miss your Medicare window.

Miss your enrollment window and the penalty doesn't go away — it rides on your premium for the rest of your life. Here's every window and deadline on a single page, with the real 2026 numbers and no hype.

  • The 7-month window — and who can safely delay past 65
  • The COBRA trap that quietly triggers a lifetime penalty
  • The Part B & Part D late penalties, in plain numbers
Free. Unsubscribe anytime. Educational only — not financial, tax, or insurance advice.

Read the full breakdown — the windows, penalties & COBRA trap →

1-page PDFMedicare timing checklist preview
Jeffrey Miller

I'm Jeffrey Miller. I break down retirement money in plain English, based on official Medicare and CMS guidance. This checklist is the same framework I use in my videos — no panic, no pitch.

This free 1-page checklist puts every Medicare window and deadline on a single page — the 7-month enrollment window, who can safely delay past 65, the COBRA trap that quietly triggers a lifetime penalty, and the Part B and Part D late penalties (with the real 2026 numbers). Want the full explanation behind it? Read the full breakdown →

Educational only — not personal financial, tax, or insurance advice. Everyone's situation is different; confirm your own dates and amounts at medicare.gov, at ssa.gov, by calling 1-800-MEDICARE, or with a licensed professional. Jeffrey Miller is an educator and is not affiliated with or endorsed by Medicare, the SSA, or any government agency.