Turning 65? Your Medicare Timeline, Month by Month

Turning 65? Here is your Medicare timeline month by month: your 7-month enrollment window, automatic vs. manual sign-up, Part A and B costs, the two lifetime penalties, working past 65, and the one-time Medigap window. ⏱ Chapters 00:00 The deadline that costs you for life 00:27 Your 7-month window 00:55 Automatic or not? 01:39 Part A & B costs in 2026 02:22 Choosing how to fill the gaps 02:57 The two penalties 03:37 Still working at 65? 04:22 The one-time Medigap window 05:01 Your checklist 🎁 Free checklist: https://drive.google.com/file/d/1tdO7... 📚 Official sources Medicare.gov — When to sign up: https://www.medicare.gov/basics/get-s... Medicare.gov — Avoid late enrollment penalties SSA — Apply for Medicare: https://www.ssa.gov/medicare CMS — 2026 premiums and deductibles SHIP free counseling: https://www.shiphelp.org Last reviewed: October 2026 Educational content only. Not affiliated with or endorsed by the U.S. government or the federal Medicare program. Not insurance, legal, tax or financial advice. We don't recommend specific plans or companies. For personalized help, contact Medicare.gov, 1-800-MEDICARE, or your local SHIP (shiphelp.org).