Medicare Has Deadlines. Miss One and the Penalties Follow You for Life.
Enrollment windows, IRMAA lookback timing, late penalties — this timeline lays out every critical Medicare date so you never get caught off guard.
What You'll Learn in This Guide
- Initial Enrollment Period — the 7-month window around your 65th birthday and why missing it triggers permanent Part B penalties of 10% per year
- IRMAA Lookback Timing — how your income from two years ago determines your Medicare premiums today, and the Form SSA-44 appeal option
- Parts A, B, C & D Deadlines — the specific enrollment windows for each part, including Annual Election Period (Oct 15–Dec 7) and Open Enrollment (Jan 1–Mar 31)
- Late Enrollment Penalties — Part B (10% per year, permanent), Part D (1% per month, permanent), and how to avoid both with creditable coverage documentation
- Medigap vs Medicare Advantage Timing — the 6-month Medigap open enrollment window after Part B starts, and why waiting can mean medical underwriting or denial
Written by Rich Ison
Fiduciary Retirement Planner
Rich works exclusively with retirees and pre-retirees in the Tampa Bay area. As a fiduciary, he coordinates Medicare planning with tax strategy — so one decision doesn't silently undermine another.
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This guide is for educational purposes only and does not constitute personalized financial or healthcare advice. Medicare rules and premiums are subject to change annually. Consult Medicare.gov or a licensed insurance professional for current information.
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