Turning 65? Your Medicare timeline, step by step.

1. 6 months before you turn 65: get organized

Make a list of your doctors, the hospitals you prefer, your prescriptions (with the dose) and your pharmacy. These decide which plans fit you best.

Still working? Find out how many employees your employer has and whether your plan is an HSA plan. It changes your timing. See working past 65.

2. 3 months before: your 7-month sign-up window opens

Your Initial Enrollment Period starts 3 months before the month you turn 65 and ends 3 months after it. If you sign up for Parts A and B in the 3 months before your birthday month, your coverage starts on the first day of your birthday month.

If you already get Social Security benefits, you’re usually enrolled in Parts A and B automatically, and your Medicare card arrives in the mail about 3 months before you turn 65. If not, apply online at SSA.gov or call Social Security at 1-800-772-1213. I’ll walk you through it, free.

Is your birthday on the 1st of the month? Then your window and coverage start one month earlier.

3. Next: choose how you get the rest of your coverage

Original Medicare (Parts A and B) doesn’t cover everything. You’ll choose one of two paths:

• Original Medicare + a Medicare Supplement + a Part D drug plan. See any doctor that accepts Medicare, with most costs covered.
• A Medicare Advantage plan. An all-in-one plan with a network, copays and a yearly out-of-pocket limit, usually with drug coverage.

See the side-by-side comparison. I’ll run your doctors and prescriptions through the actual plans in your ZIP code.

4. Your birthday month: the best time to buy a Supplement

Your Medigap Open Enrollment Period starts the month you’re 65 and enrolled in Part B, and lasts 6 months. During this window, Supplement companies can’t turn you down or charge you more because of your health. After it ends, you may have to answer health questions.

Choosing Medicare Advantage first? If you change your mind within 12 months, you have a trial period to switch to a Supplement.

5. Don’t skip drug coverage

Even if you take few or no medications, sign up for Part D (or a Medicare Advantage plan with drug coverage) when you’re first eligible, unless you have other creditable drug coverage. Going 63 days or more without it can mean a late penalty that lasts for as long as you have Part D.

6. Up to 3 months after: the window closes

You can still sign up in the 3 months after your birthday month, and coverage starts the month after you sign up. If you miss your window and don’t have job-based coverage, you’ll wait for the General Enrollment Period (January 1 – March 31) and may pay a Part B penalty of 10% for each full 12 months you were late, for as long as you have Part B.

7. Every fall after that: review your plan

Plans change every year. During Annual Enrollment, October 15 – December 7, review your coverage with my Annual Enrollment checklist, or let me do it with you.