Turning 65? Your Medicare Sign-Up Checklist

Last updated: September 29, 2026 · Anthony and Kim Insurance Agency

Signing up for Medicare for the first time can feel confusing. This checklist walks you through the main steps and deadlines.

1. Know your sign-up window

Your Initial Enrollment Period is 7 months long. It starts 3 months before the month you turn 65, includes your birthday month, and ends 3 months after. Signing up early in this window helps your coverage start without a gap.

2. Find out if you will be signed up automatically

If you are already getting Social Security or Railroad Retirement benefits, you will usually be enrolled in Part A and Part B automatically and receive your Medicare card in the mail. If not, you sign up through Social Security.

3. Still working? Check your employer coverage

If you or your spouse are still working and have health coverage through that job, you may be able to delay Part B without a penalty. The rules depend on the size of the employer and the type of coverage, so check with your employer's benefits office before you decide.

4. Avoid late penalties

• Part B: If you do not sign up when first eligible and do not have qualifying coverage, you may pay a late penalty added to your premium for as long as you have Part B.
• Part D: If you go 63 days or more in a row without Part D or other creditable drug coverage after your Initial Enrollment Period ends, you may pay a late penalty for as long as you have drug coverage.

5. Decide how you want to get your coverage

Most people choose either Original Medicare with a Medicare Supplement and a Part D drug plan, or a Medicare Advantage plan. See Medicare Advantage vs. Medicare Supplement for the main differences.

6. Gather your information

• Your Medicare card (or your Medicare number)
• A list of your doctors and preferred pharmacy
• A list of your prescriptions and doses
• Information about any current or retiree coverage

With these in hand, a licensed agent can help you compare options in just one conversation.

This article is general information about Medicare and is not advice about any specific plan. For official information, visit Medicare.gov or call 1-800-MEDICARE (TTY users 1-877-486-2048), 24 hours a day, 7 days a week.

More Medicare guides

• Medicare Advantage vs. Medicare Supplement
• Medicare Annual Enrollment Period guide