Turning 65 Medicare Checklist: A Month-by-Month Guide

Key takeaways

• Your Initial Enrollment Period is 7 months: the 3 months before the month you turn 65, your birthday month and the 3 months after.
• If you're still working with group coverage from a current job, you may be able to delay Part B and use an 8-month Special Enrollment Period later.
• Your 6-month Medigap Open Enrollment Period starts when you're 65 and have Part B, and it only happens once.

Use this turning 65 Medicare checklist to keep your dates straight. Medicare has several deadlines, and missing one can mean a gap in coverage or a penalty that lasts for years. Below is a month-by-month plan, followed by the special rules for people who are still working, have drug coverage through a job or contribute to a health savings account (HSA).

Your turning 65 Medicare checklist, month by month

4 to 6 months before your 65th birthday month

• Decide if you'll sign up now or delay. If you're retired or buy your own coverage, plan to enroll during your Initial Enrollment Period. If you're still working, see the section below.
• Ask your employer's benefits office how your plan works with Medicare. If your employer has 20 or more employees, your group plan generally pays first and Medicare pays second. With fewer than 20 employees, Medicare generally pays first.
• Find your creditable coverage notice. Your current plan must tell you each year whether its drug coverage is creditable. Keep that notice.
• Make an HSA plan if you have a health savings account. More on that below.
• List your doctors and prescriptions so you can compare coverage options.

3 months before your birthday month: your enrollment window opens

Your 7-month Initial Enrollment Period begins. If you want coverage to start right away, this is the time to sign up.

• If you qualify for Part A with no premium, it starts the month you turn 65. (If your birthday is on the first of the month, it starts the month before.)
• If you sign up for Part B before the month you turn 65, Part B starts the month you turn 65.

Your birthday month

• If you sign up for Part B during your birthday month, coverage starts the next month.
• If you already have Part B, your Medigap Open Enrollment Period begins now (see below).

1 to 3 months after your birthday month

• Your Initial Enrollment Period ends 3 months after the month you turn 65. If you sign up during this time, Part B starts the month after you sign up.
• If you miss this window and don't qualify for a Special Enrollment Period, you may have to wait to sign up, go months without coverage and pay a late penalty.

The 6 months after Part B starts

This is your Medigap Open Enrollment Period. If you want a Medicare Supplement (Medigap) policy, apply during this window. Learn how the plans differ in our guide to Medigap Plan G vs. Plan N.

Turning 65 and still working

Many people keep working past 65. If you or your spouse have group health coverage based on current employment, you may be able to delay Part B without a penalty.

You can sign up for Part B:

• Any time you're still covered by the group health plan through current or active employment, or
• During the 8-month Special Enrollment Period that begins the month after the employment or the group coverage ends, whichever happens first.

Important limits:

• COBRA and retiree plans don't count as coverage based on current employment. Your 8-month window starts when you stop working, even if you choose COBRA.
• If you want Medicare to start when your job coverage ends, Medicare.gov suggests signing up for Part B the month before you or your spouse retire. You'll also fill out a form showing you had job-based coverage.
• If your employer has fewer than 20 employees, Medicare generally pays first. In that case, talk to your benefits administrator before you delay Part B.

What happens if you miss your windows? The Part B penalty is an extra 10% for each full year you could have signed up for Part B but didn't. You'll pay it for as long as you have Part B.

Part D and creditable drug coverage

You don't have to join a Medicare drug plan right away if you have creditable drug coverage. That's coverage expected to pay, on average, at least as much as Medicare's standard drug coverage. It may come from a current or former employer or union, TRICARE or the VA.

The rule to remember is 63 days. If you go 63 days or more in a row without Medicare drug coverage or other creditable coverage after your Initial Enrollment Period, you may owe a late enrollment penalty. It's 1% of the national base beneficiary premium for each full month you went without. It's added to your premium for as long as you have Medicare drug coverage.

Keep the yearly notice your plan sends showing your drug coverage is creditable. You may need it later.

The Medigap Open Enrollment window

Your Medigap Open Enrollment Period is the 6-month period that starts the first day of the month you're 65 or older and signed up for Part B. During this time you can buy any Medigap policy sold in your state, and an insurer can't turn you down or charge you more because of health problems.

Two details matter:

• It only happens once. It doesn't repeat every year, and once it starts, it can't be changed or restarted.
• It starts with Part B, even while you're working. If you sign up for Part B while you still have employer coverage, your Medigap window starts anyway.

After the window closes, federal law no longer requires an insurer to sell you a Medigap policy, and it may cost more because of your health. Some states give extra rights.

HSA contributions stop when Medicare starts

If you have an HSA, this rule catches many people by surprise. According to the IRS, starting with the first month you're enrolled in Medicare, your HSA contribution limit is zero. That includes any months when Medicare coverage is backdated.

Here's why that matters. If you sign up for no-premium Part A after you turn 65, your coverage can start up to 6 months before the date you apply, but no earlier than the month you first became eligible. Contributions made during those backdated months count as excess contributions.

Medicare.gov's advice: you and your employer should stop contributing to your HSA 6 months before you retire or apply for Social Security or Medicare. After you enroll, you can still withdraw money already in your HSA to help pay medical expenses like deductibles, premiums, coinsurance or copayments.

The bottom line

Mark three dates on your calendar: the start of your Initial Enrollment Period, the month your Part B begins and the end of your 6-month Medigap window. If you're still working, confirm your coverage counts as current employment before you delay anything. Learn more about each part of Medicare on our Medicare parts page.

A licensed agent can build your personal timeline and compare options in your ZIP code on our Medicare page.