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Home · Medicare Readiness Timeline

Free interactive toolMedicare enrollment, mapped

When do I enroll
in Medicare?

Miss a Medicare deadline and you can pay a penalty for the rest of your life. Enter your birth month and year and we'll map your personal enrollment timeline in seconds — your Initial Enrollment Period, the one-time Medigap window, and every deadline after. No signup to see it.

Your timeline

When were you born?

We use this only to calculate your dates — nothing is saved unless you ask us to email it to you.

⚠️ Why timing matters: sign up late for Part B and you can owe a 10% penalty for every 12 months you delayed — for life. Part D has its own lifelong penalty. And the Medigap window above is the one time you can buy any supplement with no health questions asked.

Want this timeline in your inbox?

We'll email your personalized dates plus the free 2027 Coverage Changes Checklist — and a heads-up before your key window opens. Then you decide what's next, no pressure.

📅 Talk to Raymond — Free

No spam, ever. Unsubscribe anytime. English & Español.

✓ Done — check your inbox for your timeline + the free checklist. Talk soon! — Raymond