Ready Reckoner

Ready at 65

Your Medicare dates, worked out for you.

Answer a few questions. You’ll get the exact dates to sign up, what to do before each one, and how to avoid penalties that last for life.

Coming soon to iPhone and Android. Free to download.

The Dates screen in Ready at 65. It shows that the first sign-up window opens March 1, 2027, and lists every date after it.

Find your first sign-up window

Most people first sign up for Medicare during a seven-month window around their 65th birthday. Apply by the date in the last column and Parts A and B start on the first day of your birthday month. Apply later in the window and coverage starts the month after you apply.

Born in 1962

First Medicare sign-up window by birthday month
Birthday monthSign-up windowApply by
JanuaryOct 1, 2026 – Apr 30, 2027Apply by Dec 31, 2026Dec 31, 2026
FebruaryNov 1, 2026 – May 31, 2027Apply by Jan 31, 2027Jan 31, 2027
MarchDec 1, 2026 – Jun 30, 2027Apply by Feb 28, 2027Feb 28, 2027
AprilJan 1 – Jul 31, 2027Apply by Mar 31, 2027Mar 31, 2027
MayFeb 1 – Aug 31, 2027Apply by Apr 30, 2027Apr 30, 2027
JuneMar 1 – Sep 30, 2027Apply by May 31, 2027May 31, 2027
JulyApr 1 – Oct 31, 2027Apply by Jun 30, 2027Jun 30, 2027
AugustMay 1 – Nov 30, 2027Apply by Jul 31, 2027Jul 31, 2027
SeptemberJun 1 – Dec 31, 2027Apply by Aug 31, 2027Aug 31, 2027
OctoberJul 1, 2027 – Jan 31, 2028Apply by Sep 30, 2027Sep 30, 2027
NovemberAug 1, 2027 – Feb 29, 2028Apply by Oct 31, 2027Oct 31, 2027
DecemberSep 1, 2027 – Mar 31, 2028Apply by Nov 30, 2027Nov 30, 2027

Born on the 1st of the month? Use the row for the month before yours. Already getting Social Security benefits? You’ll be signed up automatically. Still working, with insurance from your job? You may be able to wait without a penalty. The app works out your exact dates in each of these cases. Sources: Medicare.gov and CMS.

What else the app does

The To do screen, with steps grouped under Before the window opens.

Steps in order

A checklist of what to do before each date, with the official link or phone number for every step.

The Learn screen, with a penalty calculator, this year’s costs and short guides.

Guides and a penalty calculator

Short guides in plain English, plus a calculator that shows what signing up late would cost each month.

The Free help screen, with a state search for SHIP counselors and phone numbers for Medicare and Social Security.

Free, unbiased help

Find your state’s SHIP counselors, who explain Medicare at no cost and don’t sell plans.

Ready at 65 Plus

One payment of $9.99, with no subscription. Your dates, steps, guides and free-help finder stay free, with or without Plus.

What’s free and what comes with Plus
FeatureFreePlus
Your personal Medicare datesIncludedIncluded
Step-by-step to-do listIncludedIncluded
Plain-English guides and a penalty calculatorIncludedIncluded
Your state’s free-help programIncludedIncluded
Reminders 30 and 7 days before each deadlineNot includedIncluded
Dates for a spouse, parent or friendNot includedIncluded
A printable plan with every date and formNot includedIncluded
Dates added to your phone’s calendarNot includedIncluded
PriceFree$9.99 once

Your answers stay on your phone

There’s no account, no tracking and no advertising. Nothing you enter is sent to us or anyone else, and the app never asks for a Medicare or Social Security number. Buying Plus goes through Apple or Google, so the app never sees your payment details.

Read the privacy policy

Independent and educational

Ready at 65 isn’t affiliated with or endorsed by Medicare, the Centers for Medicare & Medicaid Services, or the Social Security Administration. It doesn’t sell, recommend or compare plans, and signing up for Medicare is free through Social Security.

This is general information, not legal, tax or financial advice. For your own situation, talk with your state’s SHIP counselors at shiphelp.org or call 1-800-MEDICARE (1-800-633-4227).