Education / Medicare Deadlines
Medicare Deadlines
Initial Enrollment Period, late-enrollment penalties, Special Enrollment Period rules, and the small set of dates that determine whether you pay a permanent premium surcharge.
Medicare's enrollment windows look bureaucratic until they cost you. Miss the seven-month Initial Enrollment Period centered on your 65th birthday and you face a permanent 10% premium surcharge on Part B for every full year you were eligible but didn't enroll. The surcharge applies for life. A two-year delay is a 20% permanent premium increase. A four-year delay is 40%. Few one-time mistakes compound that aggressively.
This category gathers the Foundation's plain-language references for the enrollment windows that matter most: the IEP, the General Enrollment Period (your fallback if you missed the IEP), and the Special Enrollment Period that opens when employer coverage ends past 65. We pair each window with the penalty math, primary-source citations from Medicare.gov, and a one-page checklist designed to be printed and used as a yes/no decision tree.
Resources
- ArticleUpdated Sat May 02 2026 00:00:00 GMT+0000 (Coordinated Universal Time)
Medicare Enrollment Checklist (2026)
A printable, step-by-step checklist for the Initial Enrollment Period, the Special Enrollment Period, and the General Enrollment Period — designed to be worked through 12 months before age 65.
- ArticleUpdated Sat May 02 2026 00:00:00 GMT+0000 (Coordinated Universal Time)
Part B Late-Enrollment Penalty — Worked Examples
How the Part B late-enrollment penalty actually works, with calculator-style worked examples showing the lifetime cost of a 1, 3, 5, and 10-year delay.
These materials are produced by NestPilot Foundation Inc. — a 501(c)(3) public charity (filing in progress). They are free, primary-source-anchored, and never gated by an account or sales call.