Turning 65? Your Medicare Checklist (and the Deadlines That Cost Money)

Turning 65 comes with a stack of mail from insurance companies and a few deadlines that really matter. Here is the order to do things in.

Six months before you turn 65

• Create a my Social Security account at SSA.gov. You will use it to sign up and to check your records.
• Talk to HR if you are still working. Ask whether your employer has 20 or more employees and whether the plan works with Medicare. That decides whether you can delay Part B.
• List your doctors and prescriptions. You will need them to compare plans.

Three months before your birthday month

• Sign up for Part A and Part B if you are not already getting Social Security. If you already collect Social Security, you will be enrolled automatically and your card will arrive by mail.
• Decide between Original Medicare and Medicare Advantage. Original Medicare plus a Medigap policy and a Part D plan gives you any doctor that takes Medicare. Medicare Advantage bundles coverage, usually with a network and lower premiums. Our Medicare Advantage vs Original Medicare guide walks through the trade-offs.

Your first month of Part B: the Medigap window

If you choose Original Medicare, your six-month Medigap Open Enrollment Period starts the month your Part B begins. During this window, insurers must sell you any Medigap plan they offer at the best available rate, regardless of your health. After it ends, in most states they can turn you down or charge more for health conditions. See our Medigap cost guide.

Don’t forget drug coverage

Join a Part D plan (or a Medicare Advantage plan with drug coverage) when you first get Medicare, unless you have other creditable drug coverage. The late penalty is 1% of the national base premium for each month you went without coverage, and it lasts as long as you have Part D. If your income is limited, check Extra Help.

If you’re still working at 65

If you or your spouse have health coverage through current work at a company with 20 or more employees, you can usually delay Part B without a penalty. When that coverage ends, you get an eight-month Special Enrollment Period to sign up.

Two cautions:

• COBRA and retiree coverage don’t count as coverage from current work. Don’t rely on them to delay Part B.
• Health savings accounts: you can’t contribute to an HSA once you’re enrolled in any part of Medicare. Premium-free Part A can be backdated up to six months when you sign up after 65, so stop HSA contributions six months before you apply.

Costs to plan for in 2026

The standard Part B premium in 2026 is $202.90 a month, with a $283 annual deductible. Higher-income people pay more (IRMAA). The 2027 amounts are usually announced in the fall; see our Medicare costs 2027 guide for updates.

Turning 65 checklist

• Create a my Social Security account.
• Confirm whether your work coverage lets you delay Part B.
• Sign up for Parts A and B during your Initial Enrollment Period (if not automatic).
• Choose Original Medicare plus Medigap and Part D, or Medicare Advantage.
• Buy Medigap during your six-month open enrollment window if you want it.
• Enroll in drug coverage to avoid the Part D penalty.
• Watch for scams: Medicare will never call to ask for your Medicare number.

Common questions

Do I have to sign up for Medicare if I’m still working?

Usually you should take premium-free Part A. You can delay Part B if you have qualifying coverage from current work at a large employer.

Will my Medicare start on my birthday?

If you sign up before your birthday month, coverage starts the first day of your birthday month. If your birthday is on the first, it starts the month before.

Can I change my mind after choosing Medicare Advantage?

Yes. During your first year in Medicare Advantage you have a trial right to switch back to Original Medicare and buy a Medigap plan with guaranteed issue protections.